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CAS 551-16-6
(+)-6-Aminopenicillanic acid
Codes: Amoxicillin-013, Tazobactam Sodium-021, (VIII)70425-1-a, (IIIb)70425-2-a, (I)70425-3-a
Application context (from source-drug indications)
Helicobacter pylori infectionAmoxicillin/Omeprazole/RifabutinDyspepsiaAmoxicillin/Omeprazole/RifabutinIntra-abdominal infectionTazobactam Sodium/CeftolozaneVentilator-associated pneumoniaTazobactam Sodium/CeftolozaneUrinary tract infectionTazobactam Sodium/CeftolozaneCommunity-acquired bacterial pneumoniaTazobactam Sodium/CeftolozanePyelonephritisTazobactam Sodium/CeftolozaneHospital-acquired pneumoniaTazobactam Sodium/CeftolozaneDuodenal ulcerRabeprazole Sodium/Metronidazole/AmoxicillinImmune thrombocytopenic purpuraRabeprazole Sodium/Metronidazole/AmoxicillinGastric ulcerRabeprazole Sodium/Metronidazole/AmoxicillinGastritisRabeprazole Sodium/Metronidazole/AmoxicillinHelicobacter pylori infectionRabeprazole Sodium/Metronidazole/AmoxicillinMarginal zone B-cell lymphomaClarithromycin/Rabeprazole Sodium/AmoxicillinDuodenal ulcerClarithromycin/Rabeprazole Sodium/AmoxicillinImmune thrombocytopenic purpuraClarithromycin/Rabeprazole Sodium/AmoxicillinGastric ulcerClarithromycin/Rabeprazole Sodium/AmoxicillinGastritisClarithromycin/Rabeprazole Sodium/AmoxicillinHelicobacter pylori infectionClarithromycin/Rabeprazole Sodium/AmoxicillinBacterial infectionCeftazidime/Tazobactam SodiumRespiratory tract infectionCeftazidime/Tazobactam SodiumUrinary tract infectionCeftazidime/Tazobactam SodiumBacterial infectionAmoxicillin SodiumBacterial infectionTazobactam SodiumBacterial infectionFloxacillin sodium蜂窝织炎Floxacillin sodiumChronic renal impairmentFloxacillin sodium
Source drugs (routes using this intermediate)
| Drug | Tier | Expiry |
|---|---|---|
| Amoxicillin/Omeprazole/Rifabutin | Tier C — Watch / trade | - |
| Tazobactam Sodium/Ceftolozane | Tier C — Watch / trade | - |
| Rabeprazole Sodium/Metronidazole/Amoxicillin | Tier C — Watch / trade | - |
| Clarithromycin/Rabeprazole Sodium/Amoxicillin | Tier C — Watch / trade | - |
| Ceftazidime/Tazobactam Sodium | Tier C — Watch / trade | - |
| Amoxicillin Sodium | Tier C — Watch / trade | - |
| Tazobactam Sodium | Tier C — Watch / trade | - |
| Floxacillin sodium | Tier C — Watch / trade | - |
Position in synthesis routes (up/downstream chain)
Ordered by route registration; left → right is the synthesis direction. The highlighted node is the current CAS; others link to their own profiles.
Methyl glyoxylate→(S)-(-)-1-Phenylethylamine→(1S)-1-(2-Naphthyl)ethanamine→Methyl (2Z)-[[(1S)-1-phenylethyl]imino]acetate→Methyl (2Z)-[[(1S)-1-(naphthalen-2-yl)ethyl]imino]acetate→Carbolic acid→Methyl (2R)-(4-hydroxyphenyl)[(1-phenylethyl)amino]acetate→Methyl (2R)-(4-hydroxyphenyl)[[1-(naphthalen-2-yl)ethyl]amino]acetate→Methyl (2R)-(4-hydroxyphenyl)[(1-phenylethyl)amino]acetate hydrogen chloride (1/1)→Methyl (2R)-(4-hydroxyphenyl)[[1-(naphthalen-2-yl)ethyl]amino]acetate hydrogen chloride (1/1)→D-p-Hydroxyphenylglycine methyl ester hydrochloride→D-p-yHdroxyphenylglycine methyl ester→(+)-6-Aminopenicillanic acid
[[(Benzyloxy)carbonyl]amino](4-hydroxyphenyl)acetic acid→(2R)-[[(Benzyloxy)carbonyl]amino](4-hydroxyphenyl)acetic acid→(+)-6-Aminopenicillanic acid→(2S,5R,6R)-6-[[(2R)-2-[[(Benzyloxy)carbonyl]amino]-2-(4-hydroxyphenyl)acetyl]amino]-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid→Sodium (2S,5R,6R)-6-[[(2R)-2-[[(benzyloxy)carbonyl]amino]-2-(4-hydroxyphenyl)acetyl]amino]-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate
(2R)-[[(Benzyloxy)carbonyl]amino](4-hydroxyphenyl)acetic acid→(2R)-2-Amino-2-(4-hydroxyphenyl)acetic acid→1-Methoxybutane-1,3-dione→Sodium (2R)-(4-hydroxyphenyl)[[(2E)-4-methoxy-4-oxobut-2-en-2-yl]amino]acetate→Sodium (2S,5R,6R)-6-amino-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate→Potassium (2S,5R,6R)-6-amino-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate→(+)-6-Aminopenicillanic acid
(2R)-[[(Benzyloxy)carbonyl]amino](4-hydroxyphenyl)acetic acid→(2R)-[[(Benzyloxy)carbonyl]amino](4-[[(benzyloxy)carbonyl]oxy]phenyl)acetic acid→(+)-6-Aminopenicillanic acid→(2S,5R,6R)-6-[[(2R)-2-Amino-2-(4-[[(benzyloxy)carbonyl]oxy]phenyl)acetyl]amino]-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid→(2R)-2-Amino-2-(4-hydroxyphenyl)acetic acid→(2R)-Amino(4-hydroxyphenyl)acetyl chloride hydrogen chloride
[[(Benzyloxy)carbonyl]amino](4-[[(benzyloxy)carbonyl]oxy]phenyl)acetic acid→(+)-6-Aminopenicillanic acid→(2S,5R,6R)-6-[[[[(Benzyloxy)carbonyl]amino](4-[[(benzyloxy)carbonyl]oxy]phenyl)acetyl]amino]-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid→Sodium (2S,5R,6R)-6-[[[[(benzyloxy)carbonyl]amino](4-[[(benzyloxy)carbonyl]oxy]phenyl)acetyl]amino]-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate→(2S,5R,6R)-6-[[Amino(4-hydroxyphenyl)acetyl]amino]-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid
(2R)-2-Amino-2-(4-hydroxyphenyl)acetic acid→(2R)-([[(9H-Fluoren-9-yl)methoxy]carbonyl]amino)(4-hydroxyphenyl)acetic acid→(+)-6-Aminopenicillanic acid→(2S,5R,6R)-6-[[(2R)-2-([[(9H-Fluoren-9-yl)methoxy]carbonyl]amino)-2-(4-hydroxyphenyl)acetyl]amino]-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid
(+)-6-Aminopenicillanic acid→(2S,5R)-6,6-Dibromo-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid→Diphenylmethyl (2S,5R)-6,6-dibromo-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate→Diphenylmethyl (2S,5R)-6,6-dibromo-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate 4-oxide→(2S,5R)-2beta-[(Benzhydryloxy)carbonyl]-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane4-oxide→Methyl (2S,5R)-3,3-dimethyl-4,7-dioxo-4lambda4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate→1-(Trimethylsilyl)-1,2,3-triazole→1,2,3-Triazole→3-(1,2,3-Triazol-4-yl)pyridine→(2S,3S,5R)-2-Methyl-2-(1H-1,2,3-triazol-1-ylmethyl)penam-3-carboxylic acid diphenylmethyl ester→Methyl (2S,3S,5R)-3-methyl-7-oxo-3-[(1H-1,2,3-triazol-1-yl)methyl]-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate→(2S,4R,6S)-6-Bromo-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid 4-oxide→(Diphenylmethylidene)hydrazine→(2S,5R)-3,3-Dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid→(2S,5R)-3,3-Dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid 4-oxide→Benzhydryl (2S,5R)-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate→1,3-Benzothiazole-2-thiol→(2R)-2-[(2R)-2-[(Benzothiazol-2-yl)dithio]-4-oxoazetidin-1-yl]-3-methyl-3-butenoic acid benzhydryl ester→Methyl (2R)-2-[(2R)-2-[(1,3-benzothiazol-2-yl)disulfanyl]-4-oxoazetidin-1-yl]-3-methylbut-3-enoate→Diphenylmethyl (2S,3R,5R)-3-(bromomethyl)-3-methyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate→(2S-(2alpha,3beta,5alpha))-3-(Chloromethyl)-3-methyl-7-oxo-4-thia-1-azabicyclo(3.2.0)heptane-2-carboxylic acid diphenylmethyl ester→Methyl (2S,3R,5R)-3-(chloromethyl)-3-methyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate
(+)-6-Aminopenicillanic acid→(2S,5R,6S)-6-Bromo-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid→(2S,4R,6S)-6-Bromo-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid 4-oxide→(Diphenylmethylidene)hydrazine→[Diazo(phenyl)methyl]benzene→(2S,5R,6S)-Benzhydryl 6-bromo-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate 4-oxide→Diphenylmethyl (2S,5R,6S)-6-bromo-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate→(2S,5R)-2beta-[(Benzhydryloxy)carbonyl]-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane4-oxide→1,3-Benzothiazole-2-thiol→(2R)-2-[(2R)-2-[(Benzothiazol-2-yl)dithio]-4-oxoazetidin-1-yl]-3-methyl-3-butenoic acid benzhydryl ester→(2S-(2alpha,3beta,5alpha))-3-(Chloromethyl)-3-methyl-7-oxo-4-thia-1-azabicyclo(3.2.0)heptane-2-carboxylic acid diphenylmethyl ester→Diphenylmethyl (2S,3R,4R,5R)-3-(chloromethyl)-3-methyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate 4-oxide→Diphenylmethyl (2S,3S,4R,5R)-3-(azidomethyl)-3-methyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate 4-oxide→Benzhydryl (2S,3S,5R)-3-(azidomethyl)-3-methyl-4,4,7-trioxo-4lambda6-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate→Diphenylmethyl (2R,3S,6R)-3-azido-3-methyl-8-oxo-5-thia-1-azabicyclo[4.2.0]octane-2-carboxylate→Benzhydryl (2S,3S,5R)-3-(azidomethyl)-3-methyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate→Acetylene→Benzhydryl (2S,3S,5R)-3-((1H-1,2,3-triazol-1-yl)methyl)-3-methyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate 4,4-dioxide→(2S,3S,5R)-3-Methyl-4,4,7-trioxo-3-(triazol-1-ylmethyl)-4lambda6-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid
(+)-6-Aminopenicillanic acid→(Diphenylmethylidene)hydrazine→(2S,5R)-2beta-[(Benzhydryloxy)carbonyl]-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane4-oxide→Diphenylmethyl (2S,4R,5R,6R)-6-amino-3,3-dimethyl-4,7-dioxo-4lambda4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate→(2S,5R,6R)-6-[(tert-Butoxycarbonyl)amino]-3,3-dimethyl-4,7-dioxo-4lambda4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid→Diphenylmethyl (2S,5R,6R)-6-[(tert-butoxycarbonyl)amino]-3,3-dimethyl-4,7-dioxo-4lambda4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate
Methyl glyoxylate→(S)-(-)-1-Phenylethylamine→(1S)-1-(2-Naphthyl)ethanamine→Methyl (2Z)-[[(1S)-1-phenylethyl]imino]acetate→Methyl (2Z)-[[(1S)-1-(naphthalen-2-yl)ethyl]imino]acetate→Carbolic acid→Methyl (2R)-(4-hydroxyphenyl)[(1-phenylethyl)amino]acetate→Methyl (2R)-(4-hydroxyphenyl)[[1-(naphthalen-2-yl)ethyl]amino]acetate→Methyl (2R)-(4-hydroxyphenyl)[(1-phenylethyl)amino]acetate hydrogen chloride (1/1)→Methyl (2R)-(4-hydroxyphenyl)[[1-(naphthalen-2-yl)ethyl]amino]acetate hydrogen chloride (1/1)→D-p-Hydroxyphenylglycine methyl ester hydrochloride→D-p-yHdroxyphenylglycine methyl ester→(+)-6-Aminopenicillanic acid
[[(Benzyloxy)carbonyl]amino](4-hydroxyphenyl)acetic acid→(2R)-[[(Benzyloxy)carbonyl]amino](4-hydroxyphenyl)acetic acid→(+)-6-Aminopenicillanic acid→(2S,5R,6R)-6-[[(2R)-2-[[(Benzyloxy)carbonyl]amino]-2-(4-hydroxyphenyl)acetyl]amino]-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid→Sodium (2S,5R,6R)-6-[[(2R)-2-[[(benzyloxy)carbonyl]amino]-2-(4-hydroxyphenyl)acetyl]amino]-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate
(2R)-[[(Benzyloxy)carbonyl]amino](4-hydroxyphenyl)acetic acid→(2R)-2-Amino-2-(4-hydroxyphenyl)acetic acid→1-Methoxybutane-1,3-dione→Sodium (2R)-(4-hydroxyphenyl)[[(2E)-4-methoxy-4-oxobut-2-en-2-yl]amino]acetate→Sodium (2S,5R,6R)-6-amino-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate→Potassium (2S,5R,6R)-6-amino-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate→(+)-6-Aminopenicillanic acid
(2R)-[[(Benzyloxy)carbonyl]amino](4-hydroxyphenyl)acetic acid→(2R)-[[(Benzyloxy)carbonyl]amino](4-[[(benzyloxy)carbonyl]oxy]phenyl)acetic acid→(+)-6-Aminopenicillanic acid→(2S,5R,6R)-6-[[(2R)-2-Amino-2-(4-[[(benzyloxy)carbonyl]oxy]phenyl)acetyl]amino]-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid→(2R)-2-Amino-2-(4-hydroxyphenyl)acetic acid→(2R)-Amino(4-hydroxyphenyl)acetyl chloride hydrogen chloride
[[(Benzyloxy)carbonyl]amino](4-[[(benzyloxy)carbonyl]oxy]phenyl)acetic acid→(+)-6-Aminopenicillanic acid→(2S,5R,6R)-6-[[[[(Benzyloxy)carbonyl]amino](4-[[(benzyloxy)carbonyl]oxy]phenyl)acetyl]amino]-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid→Sodium (2S,5R,6R)-6-[[[[(benzyloxy)carbonyl]amino](4-[[(benzyloxy)carbonyl]oxy]phenyl)acetyl]amino]-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate→(2S,5R,6R)-6-[[Amino(4-hydroxyphenyl)acetyl]amino]-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid
(2R)-2-Amino-2-(4-hydroxyphenyl)acetic acid→(2R)-([[(9H-Fluoren-9-yl)methoxy]carbonyl]amino)(4-hydroxyphenyl)acetic acid→(+)-6-Aminopenicillanic acid→(2S,5R,6R)-6-[[(2R)-2-([[(9H-Fluoren-9-yl)methoxy]carbonyl]amino)-2-(4-hydroxyphenyl)acetyl]amino]-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid
Methyl glyoxylate→(S)-(-)-1-Phenylethylamine→(1S)-1-(2-Naphthyl)ethanamine→Methyl (2Z)-[[(1S)-1-phenylethyl]imino]acetate→Methyl (2Z)-[[(1S)-1-(naphthalen-2-yl)ethyl]imino]acetate→Carbolic acid→Methyl (2R)-(4-hydroxyphenyl)[(1-phenylethyl)amino]acetate→Methyl (2R)-(4-hydroxyphenyl)[[1-(naphthalen-2-yl)ethyl]amino]acetate→Methyl (2R)-(4-hydroxyphenyl)[(1-phenylethyl)amino]acetate hydrogen chloride (1/1)→Methyl (2R)-(4-hydroxyphenyl)[[1-(naphthalen-2-yl)ethyl]amino]acetate hydrogen chloride (1/1)→D-p-Hydroxyphenylglycine methyl ester hydrochloride→D-p-yHdroxyphenylglycine methyl ester→(+)-6-Aminopenicillanic acid
[[(Benzyloxy)carbonyl]amino](4-hydroxyphenyl)acetic acid→(2R)-[[(Benzyloxy)carbonyl]amino](4-hydroxyphenyl)acetic acid→(+)-6-Aminopenicillanic acid→(2S,5R,6R)-6-[[(2R)-2-[[(Benzyloxy)carbonyl]amino]-2-(4-hydroxyphenyl)acetyl]amino]-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid→Sodium (2S,5R,6R)-6-[[(2R)-2-[[(benzyloxy)carbonyl]amino]-2-(4-hydroxyphenyl)acetyl]amino]-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate
(2R)-[[(Benzyloxy)carbonyl]amino](4-hydroxyphenyl)acetic acid→(2R)-2-Amino-2-(4-hydroxyphenyl)acetic acid→1-Methoxybutane-1,3-dione→Sodium (2R)-(4-hydroxyphenyl)[[(2E)-4-methoxy-4-oxobut-2-en-2-yl]amino]acetate→Sodium (2S,5R,6R)-6-amino-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate→Potassium (2S,5R,6R)-6-amino-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate→(+)-6-Aminopenicillanic acid
(2R)-[[(Benzyloxy)carbonyl]amino](4-hydroxyphenyl)acetic acid→(2R)-[[(Benzyloxy)carbonyl]amino](4-[[(benzyloxy)carbonyl]oxy]phenyl)acetic acid→(+)-6-Aminopenicillanic acid→(2S,5R,6R)-6-[[(2R)-2-Amino-2-(4-[[(benzyloxy)carbonyl]oxy]phenyl)acetyl]amino]-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid→(2R)-2-Amino-2-(4-hydroxyphenyl)acetic acid→(2R)-Amino(4-hydroxyphenyl)acetyl chloride hydrogen chloride
[[(Benzyloxy)carbonyl]amino](4-[[(benzyloxy)carbonyl]oxy]phenyl)acetic acid→(+)-6-Aminopenicillanic acid→(2S,5R,6R)-6-[[[[(Benzyloxy)carbonyl]amino](4-[[(benzyloxy)carbonyl]oxy]phenyl)acetyl]amino]-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid→Sodium (2S,5R,6R)-6-[[[[(benzyloxy)carbonyl]amino](4-[[(benzyloxy)carbonyl]oxy]phenyl)acetyl]amino]-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate→(2S,5R,6R)-6-[[Amino(4-hydroxyphenyl)acetyl]amino]-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid
(2R)-2-Amino-2-(4-hydroxyphenyl)acetic acid→(2R)-([[(9H-Fluoren-9-yl)methoxy]carbonyl]amino)(4-hydroxyphenyl)acetic acid→(+)-6-Aminopenicillanic acid→(2S,5R,6R)-6-[[(2R)-2-([[(9H-Fluoren-9-yl)methoxy]carbonyl]amino)-2-(4-hydroxyphenyl)acetyl]amino]-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid
(+)-6-Aminopenicillanic acid→(2S,5R)-6,6-Dibromo-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid→Diphenylmethyl (2S,5R)-6,6-dibromo-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate→Diphenylmethyl (2S,5R)-6,6-dibromo-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate 4-oxide→(2S,5R)-2beta-[(Benzhydryloxy)carbonyl]-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane4-oxide→Methyl (2S,5R)-3,3-dimethyl-4,7-dioxo-4lambda4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate→1-(Trimethylsilyl)-1,2,3-triazole→1,2,3-Triazole→3-(1,2,3-Triazol-4-yl)pyridine→(2S,3S,5R)-2-Methyl-2-(1H-1,2,3-triazol-1-ylmethyl)penam-3-carboxylic acid diphenylmethyl ester→Methyl (2S,3S,5R)-3-methyl-7-oxo-3-[(1H-1,2,3-triazol-1-yl)methyl]-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate→(2S,4R,6S)-6-Bromo-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid 4-oxide→(Diphenylmethylidene)hydrazine→(2S,5R)-3,3-Dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid→(2S,5R)-3,3-Dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid 4-oxide→Benzhydryl (2S,5R)-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate→1,3-Benzothiazole-2-thiol→(2R)-2-[(2R)-2-[(Benzothiazol-2-yl)dithio]-4-oxoazetidin-1-yl]-3-methyl-3-butenoic acid benzhydryl ester→Methyl (2R)-2-[(2R)-2-[(1,3-benzothiazol-2-yl)disulfanyl]-4-oxoazetidin-1-yl]-3-methylbut-3-enoate→Diphenylmethyl (2S,3R,5R)-3-(bromomethyl)-3-methyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate→(2S-(2alpha,3beta,5alpha))-3-(Chloromethyl)-3-methyl-7-oxo-4-thia-1-azabicyclo(3.2.0)heptane-2-carboxylic acid diphenylmethyl ester→Methyl (2S,3R,5R)-3-(chloromethyl)-3-methyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate
(+)-6-Aminopenicillanic acid→(2S,5R,6S)-6-Bromo-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid→(2S,4R,6S)-6-Bromo-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid 4-oxide→(Diphenylmethylidene)hydrazine→[Diazo(phenyl)methyl]benzene→(2S,5R,6S)-Benzhydryl 6-bromo-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate 4-oxide→Diphenylmethyl (2S,5R,6S)-6-bromo-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate→(2S,5R)-2beta-[(Benzhydryloxy)carbonyl]-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane4-oxide→1,3-Benzothiazole-2-thiol→(2R)-2-[(2R)-2-[(Benzothiazol-2-yl)dithio]-4-oxoazetidin-1-yl]-3-methyl-3-butenoic acid benzhydryl ester→(2S-(2alpha,3beta,5alpha))-3-(Chloromethyl)-3-methyl-7-oxo-4-thia-1-azabicyclo(3.2.0)heptane-2-carboxylic acid diphenylmethyl ester→Diphenylmethyl (2S,3R,4R,5R)-3-(chloromethyl)-3-methyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate 4-oxide→Diphenylmethyl (2S,3S,4R,5R)-3-(azidomethyl)-3-methyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate 4-oxide→Benzhydryl (2S,3S,5R)-3-(azidomethyl)-3-methyl-4,4,7-trioxo-4lambda6-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate→Diphenylmethyl (2R,3S,6R)-3-azido-3-methyl-8-oxo-5-thia-1-azabicyclo[4.2.0]octane-2-carboxylate→Benzhydryl (2S,3S,5R)-3-(azidomethyl)-3-methyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate→Acetylene→Benzhydryl (2S,3S,5R)-3-((1H-1,2,3-triazol-1-yl)methyl)-3-methyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate 4,4-dioxide→(2S,3S,5R)-3-Methyl-4,4,7-trioxo-3-(triazol-1-ylmethyl)-4lambda6-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid
(+)-6-Aminopenicillanic acid→(Diphenylmethylidene)hydrazine→(2S,5R)-2beta-[(Benzhydryloxy)carbonyl]-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane4-oxide→Diphenylmethyl (2S,4R,5R,6R)-6-amino-3,3-dimethyl-4,7-dioxo-4lambda4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate→(2S,5R,6R)-6-[(tert-Butoxycarbonyl)amino]-3,3-dimethyl-4,7-dioxo-4lambda4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid→Diphenylmethyl (2S,5R,6R)-6-[(tert-butoxycarbonyl)amino]-3,3-dimethyl-4,7-dioxo-4lambda4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate
Methyl glyoxylate→(S)-(-)-1-Phenylethylamine→(1S)-1-(2-Naphthyl)ethanamine→Methyl (2Z)-[[(1S)-1-phenylethyl]imino]acetate→Methyl (2Z)-[[(1S)-1-(naphthalen-2-yl)ethyl]imino]acetate→Carbolic acid→Methyl (2R)-(4-hydroxyphenyl)[(1-phenylethyl)amino]acetate→Methyl (2R)-(4-hydroxyphenyl)[[1-(naphthalen-2-yl)ethyl]amino]acetate→Methyl (2R)-(4-hydroxyphenyl)[(1-phenylethyl)amino]acetate hydrogen chloride (1/1)→Methyl (2R)-(4-hydroxyphenyl)[[1-(naphthalen-2-yl)ethyl]amino]acetate hydrogen chloride (1/1)→D-p-Hydroxyphenylglycine methyl ester hydrochloride→D-p-yHdroxyphenylglycine methyl ester→(+)-6-Aminopenicillanic acid
[[(Benzyloxy)carbonyl]amino](4-hydroxyphenyl)acetic acid→(2R)-[[(Benzyloxy)carbonyl]amino](4-hydroxyphenyl)acetic acid→(+)-6-Aminopenicillanic acid→(2S,5R,6R)-6-[[(2R)-2-[[(Benzyloxy)carbonyl]amino]-2-(4-hydroxyphenyl)acetyl]amino]-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid→Sodium (2S,5R,6R)-6-[[(2R)-2-[[(benzyloxy)carbonyl]amino]-2-(4-hydroxyphenyl)acetyl]amino]-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate
(2R)-[[(Benzyloxy)carbonyl]amino](4-hydroxyphenyl)acetic acid→(2R)-2-Amino-2-(4-hydroxyphenyl)acetic acid→1-Methoxybutane-1,3-dione→Sodium (2R)-(4-hydroxyphenyl)[[(2E)-4-methoxy-4-oxobut-2-en-2-yl]amino]acetate→Sodium (2S,5R,6R)-6-amino-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate→Potassium (2S,5R,6R)-6-amino-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate→(+)-6-Aminopenicillanic acid
(2R)-[[(Benzyloxy)carbonyl]amino](4-hydroxyphenyl)acetic acid→(2R)-[[(Benzyloxy)carbonyl]amino](4-[[(benzyloxy)carbonyl]oxy]phenyl)acetic acid→(+)-6-Aminopenicillanic acid→(2S,5R,6R)-6-[[(2R)-2-Amino-2-(4-[[(benzyloxy)carbonyl]oxy]phenyl)acetyl]amino]-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid→(2R)-2-Amino-2-(4-hydroxyphenyl)acetic acid→(2R)-Amino(4-hydroxyphenyl)acetyl chloride hydrogen chloride
[[(Benzyloxy)carbonyl]amino](4-[[(benzyloxy)carbonyl]oxy]phenyl)acetic acid→(+)-6-Aminopenicillanic acid→(2S,5R,6R)-6-[[[[(Benzyloxy)carbonyl]amino](4-[[(benzyloxy)carbonyl]oxy]phenyl)acetyl]amino]-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid→Sodium (2S,5R,6R)-6-[[[[(benzyloxy)carbonyl]amino](4-[[(benzyloxy)carbonyl]oxy]phenyl)acetyl]amino]-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate→(2S,5R,6R)-6-[[Amino(4-hydroxyphenyl)acetyl]amino]-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid
(2R)-2-Amino-2-(4-hydroxyphenyl)acetic acid→(2R)-([[(9H-Fluoren-9-yl)methoxy]carbonyl]amino)(4-hydroxyphenyl)acetic acid→(+)-6-Aminopenicillanic acid→(2S,5R,6R)-6-[[(2R)-2-([[(9H-Fluoren-9-yl)methoxy]carbonyl]amino)-2-(4-hydroxyphenyl)acetyl]amino]-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid
(+)-6-Aminopenicillanic acid→(2S,5R)-6,6-Dibromo-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid→Diphenylmethyl (2S,5R)-6,6-dibromo-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate→Diphenylmethyl (2S,5R)-6,6-dibromo-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate 4-oxide→(2S,5R)-2beta-[(Benzhydryloxy)carbonyl]-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane4-oxide→Methyl (2S,5R)-3,3-dimethyl-4,7-dioxo-4lambda4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate→1-(Trimethylsilyl)-1,2,3-triazole→1,2,3-Triazole→3-(1,2,3-Triazol-4-yl)pyridine→(2S,3S,5R)-2-Methyl-2-(1H-1,2,3-triazol-1-ylmethyl)penam-3-carboxylic acid diphenylmethyl ester→Methyl (2S,3S,5R)-3-methyl-7-oxo-3-[(1H-1,2,3-triazol-1-yl)methyl]-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate→(2S,4R,6S)-6-Bromo-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid 4-oxide→(Diphenylmethylidene)hydrazine→(2S,5R)-3,3-Dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid→(2S,5R)-3,3-Dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid 4-oxide→Benzhydryl (2S,5R)-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate→1,3-Benzothiazole-2-thiol→(2R)-2-[(2R)-2-[(Benzothiazol-2-yl)dithio]-4-oxoazetidin-1-yl]-3-methyl-3-butenoic acid benzhydryl ester→Methyl (2R)-2-[(2R)-2-[(1,3-benzothiazol-2-yl)disulfanyl]-4-oxoazetidin-1-yl]-3-methylbut-3-enoate→Diphenylmethyl (2S,3R,5R)-3-(bromomethyl)-3-methyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate→(2S-(2alpha,3beta,5alpha))-3-(Chloromethyl)-3-methyl-7-oxo-4-thia-1-azabicyclo(3.2.0)heptane-2-carboxylic acid diphenylmethyl ester→Methyl (2S,3R,5R)-3-(chloromethyl)-3-methyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate
(+)-6-Aminopenicillanic acid→(2S,5R,6S)-6-Bromo-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid→(2S,4R,6S)-6-Bromo-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid 4-oxide→(Diphenylmethylidene)hydrazine→[Diazo(phenyl)methyl]benzene→(2S,5R,6S)-Benzhydryl 6-bromo-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate 4-oxide→Diphenylmethyl (2S,5R,6S)-6-bromo-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate→(2S,5R)-2beta-[(Benzhydryloxy)carbonyl]-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane4-oxide→1,3-Benzothiazole-2-thiol→(2R)-2-[(2R)-2-[(Benzothiazol-2-yl)dithio]-4-oxoazetidin-1-yl]-3-methyl-3-butenoic acid benzhydryl ester→(2S-(2alpha,3beta,5alpha))-3-(Chloromethyl)-3-methyl-7-oxo-4-thia-1-azabicyclo(3.2.0)heptane-2-carboxylic acid diphenylmethyl ester→Diphenylmethyl (2S,3R,4R,5R)-3-(chloromethyl)-3-methyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate 4-oxide→Diphenylmethyl (2S,3S,4R,5R)-3-(azidomethyl)-3-methyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate 4-oxide→Benzhydryl (2S,3S,5R)-3-(azidomethyl)-3-methyl-4,4,7-trioxo-4lambda6-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate→Diphenylmethyl (2R,3S,6R)-3-azido-3-methyl-8-oxo-5-thia-1-azabicyclo[4.2.0]octane-2-carboxylate→Benzhydryl (2S,3S,5R)-3-(azidomethyl)-3-methyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate→Acetylene→Benzhydryl (2S,3S,5R)-3-((1H-1,2,3-triazol-1-yl)methyl)-3-methyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate 4,4-dioxide→(2S,3S,5R)-3-Methyl-4,4,7-trioxo-3-(triazol-1-ylmethyl)-4lambda6-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid
(+)-6-Aminopenicillanic acid→(Diphenylmethylidene)hydrazine→(2S,5R)-2beta-[(Benzhydryloxy)carbonyl]-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane4-oxide→Diphenylmethyl (2S,4R,5R,6R)-6-amino-3,3-dimethyl-4,7-dioxo-4lambda4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate→(2S,5R,6R)-6-[(tert-Butoxycarbonyl)amino]-3,3-dimethyl-4,7-dioxo-4lambda4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid→Diphenylmethyl (2S,5R,6R)-6-[(tert-butoxycarbonyl)amino]-3,3-dimethyl-4,7-dioxo-4lambda4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate
2-Chloro-6-fluorobenzaldehyde→2-Chloro-6-fluorobenzaldehyde oxime→2-Chloro-6-fluoro-N-hydroxybenzenecarboximidoyl chloride→1-Methoxybutane-1,3-dione→Methyl 3-(2-chloro-6-fluorophenyl)-5-methyl-1,2-oxazole-4-carboxylate→3-(2-chloro-6-fluorophenyl)-5-methyl-1,2-oxazole-4-carboxylic acid→3-(2-chloro-6-fluorophenyl)-5-methyl-1,2-oxazole-4-carbonyl chloride→(+)-6-Aminopenicillanic acid
3-(2-chloro-6-fluorophenyl)-5-methyl-1,2-oxazole-4-carboxylic acid→3-(2-Chloro-6-fluorophenyl)-5-methyl-1,2-oxazole-4-carboxylic 2,2-dimethylpropanoic anhydride→S-1,3-Benzothiazol-2-yl 3-(2-chloro-6-fluorophenyl)-5-methyl-1,2-oxazole-4-carbothioate→(2S,5R,6R)-6-Amino-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid - N,N-diethylethanamine→(+)-6-Aminopenicillanic acid→(2S,5R,6R)-6-([[3-(2-Chloro-6-fluorophenyl)-5-methyl-1,2-oxazol-4-yl]carbonyl]amino)-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid - N,N-diethylethanamine→(2S,5R,6R)-6-([[3-(2-Chloro-6-fluorophenyl)-5-methyl-1,2-oxazol-4-yl]carbonyl]amino)-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid
(+)-6-Aminopenicillanic acid→Sodium (2S,5R,6R)-6-amino-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate→Potassium (2S,5R,6R)-6-amino-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate→3-(2-chloro-6-fluorophenyl)-5-methyl-1,2-oxazole-4-carbonyl chloride→(2S,5R,6R)-6-([[3-(2-Chloro-6-fluorophenyl)-5-methyl-1,2-oxazol-4-yl]carbonyl]amino)-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid
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