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CAS 80353-26-0

(2S,5R,6S)-Benzhydryl 6-bromo-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate 4-oxide

Codes: Tazobactam Sodium-045

Application context (from source-drug indications)

Intra-abdominal infectionTazobactam Sodium/CeftolozaneVentilator-associated pneumoniaTazobactam Sodium/CeftolozaneUrinary tract infectionTazobactam Sodium/CeftolozaneCommunity-acquired bacterial pneumoniaTazobactam Sodium/CeftolozanePyelonephritisTazobactam Sodium/CeftolozaneHospital-acquired pneumoniaTazobactam Sodium/CeftolozaneBacterial infectionCeftazidime/Tazobactam SodiumRespiratory tract infectionCeftazidime/Tazobactam SodiumUrinary tract infectionCeftazidime/Tazobactam SodiumBacterial infectionTazobactam Sodium

Source drugs (routes using this intermediate)

DrugTierExpiry
Tazobactam Sodium/CeftolozaneTier C — Watch / trade-
Ceftazidime/Tazobactam SodiumTier C — Watch / trade-
Tazobactam SodiumTier 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.

Tazobactam Sodium/CeftolozaneOptimised routesteps: 15total yield: 4.6g(Tazobactam (Free))
(+)-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
Ceftazidime/Tazobactam SodiumOptimised routesteps: 15total yield: 4.6g(Tazobactam (Free))
(+)-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
Tazobactam SodiumOptimised routesteps: 15total yield: 4.6g(Tazobactam (Free))
(+)-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

Intermediates available on this site

Side-by-side comparison of all listed offers on this CAS; price bands are list-price ranges, final price subject to RFQ confirmation.

SupplierProductPrice bandMOQLead timeQualificationsAction
Unibest Taizhou GMP-like SiteBENZHYDRYL 6,6-DIHYDROPENICILLIC ACID 1-OXIDE[TAZOBACTAM INTERMEDIATE]
Pharmaceutical Intermediates
On requestOn requestOn request
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