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CAS 2375589-54-9

Benzyl (2R)-2-[(2R)-2-[(1,3-benzothiazol-2-yl)disulfanyl]-4-oxoazetidin-1-yl]-3-methylbut-3-enoate

Codes: Tazobactam Sodium-062

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: 9total yield: 7.4g(Tazobactam (Free))
(2S,4R,6S)-6-Bromo-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid 4-oxide→1-(Chloromethyl)-3,5-dinitrobenzene→1-Methyl-3,5-dinitrobenzene→Benzyl (2S,4R,5R,6S)-6-bromo-3,3-dimethyl-4,7-dioxo-4lambda4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate→(3,5-Dinitrophenyl)methyl (2S,4R,5R,6S)-6-bromo-3,3-dimethyl-4,7-dioxo-4lambda4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate→Benzyl (2S,4R,5R)-3,3-dimethyl-4,7-dioxo-4lambda4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate→(3,5-Dinitrophenyl)methyl (2S,4R,5R)-3,3-dimethyl-4,7-dioxo-4lambda4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate→1,3-Benzothiazole-2-thiol→Benzyl (2R)-2-[(2R)-2-[(1,3-benzothiazol-2-yl)disulfanyl]-4-oxoazetidin-1-yl]-3-methylbut-3-enoate→(3,5-Dinitrophenyl)methyl (2R)-2-[(2R)-2-[(1,3-benzothiazol-2-yl)disulfanyl]-4-oxoazetidin-1-yl]-3-methylbut-3-enoate→Benzyl (2S,3R,5R)-3-(chloromethyl)-3-methyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate→(3,5-Dinitrophenyl)methyl (2S,3R,5R)-3-(chloromethyl)-3-methyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate→Benzyl (2S,3S,5R)-3-(azidomethyl)-3-methyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate→(3,5-Dinitrophenyl)methyl (2S,3S,5R)-3-(azidomethyl)-3-methyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate→Benzyl (2S,3S,5R)-3-(azidomethyl)-3-methyl-4,4,7-trioxo-4lambda6-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate→(3,5-Dinitrophenyl)methyl (2S,3S,5R)-3-(azidomethyl)-3-methyl-4,4,7-trioxo-4lambda6-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate→Acetylene→Benzyl (2S,3S,5R)-3-methyl-4,4,7-trioxo-3-[(1H-1,2,3-triazol-1-yl)methyl]-4lambda6-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate→(3,5-Dinitrophenyl)methyl (2S,3S,5R)-3-methyl-4,4,7-trioxo-3-[(1H-1,2,3-triazol-1-yl)methyl]-4lambda6-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate→(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: 9total yield: 7.4g(Tazobactam (Free))
(2S,4R,6S)-6-Bromo-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid 4-oxide→1-(Chloromethyl)-3,5-dinitrobenzene→1-Methyl-3,5-dinitrobenzene→Benzyl (2S,4R,5R,6S)-6-bromo-3,3-dimethyl-4,7-dioxo-4lambda4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate→(3,5-Dinitrophenyl)methyl (2S,4R,5R,6S)-6-bromo-3,3-dimethyl-4,7-dioxo-4lambda4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate→Benzyl (2S,4R,5R)-3,3-dimethyl-4,7-dioxo-4lambda4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate→(3,5-Dinitrophenyl)methyl (2S,4R,5R)-3,3-dimethyl-4,7-dioxo-4lambda4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate→1,3-Benzothiazole-2-thiol→Benzyl (2R)-2-[(2R)-2-[(1,3-benzothiazol-2-yl)disulfanyl]-4-oxoazetidin-1-yl]-3-methylbut-3-enoate→(3,5-Dinitrophenyl)methyl (2R)-2-[(2R)-2-[(1,3-benzothiazol-2-yl)disulfanyl]-4-oxoazetidin-1-yl]-3-methylbut-3-enoate→Benzyl (2S,3R,5R)-3-(chloromethyl)-3-methyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate→(3,5-Dinitrophenyl)methyl (2S,3R,5R)-3-(chloromethyl)-3-methyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate→Benzyl (2S,3S,5R)-3-(azidomethyl)-3-methyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate→(3,5-Dinitrophenyl)methyl (2S,3S,5R)-3-(azidomethyl)-3-methyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate→Benzyl (2S,3S,5R)-3-(azidomethyl)-3-methyl-4,4,7-trioxo-4lambda6-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate→(3,5-Dinitrophenyl)methyl (2S,3S,5R)-3-(azidomethyl)-3-methyl-4,4,7-trioxo-4lambda6-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate→Acetylene→Benzyl (2S,3S,5R)-3-methyl-4,4,7-trioxo-3-[(1H-1,2,3-triazol-1-yl)methyl]-4lambda6-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate→(3,5-Dinitrophenyl)methyl (2S,3S,5R)-3-methyl-4,4,7-trioxo-3-[(1H-1,2,3-triazol-1-yl)methyl]-4lambda6-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate→(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: 9total yield: 7.4g(Tazobactam (Free))
(2S,4R,6S)-6-Bromo-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid 4-oxide→1-(Chloromethyl)-3,5-dinitrobenzene→1-Methyl-3,5-dinitrobenzene→Benzyl (2S,4R,5R,6S)-6-bromo-3,3-dimethyl-4,7-dioxo-4lambda4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate→(3,5-Dinitrophenyl)methyl (2S,4R,5R,6S)-6-bromo-3,3-dimethyl-4,7-dioxo-4lambda4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate→Benzyl (2S,4R,5R)-3,3-dimethyl-4,7-dioxo-4lambda4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate→(3,5-Dinitrophenyl)methyl (2S,4R,5R)-3,3-dimethyl-4,7-dioxo-4lambda4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate→1,3-Benzothiazole-2-thiol→Benzyl (2R)-2-[(2R)-2-[(1,3-benzothiazol-2-yl)disulfanyl]-4-oxoazetidin-1-yl]-3-methylbut-3-enoate→(3,5-Dinitrophenyl)methyl (2R)-2-[(2R)-2-[(1,3-benzothiazol-2-yl)disulfanyl]-4-oxoazetidin-1-yl]-3-methylbut-3-enoate→Benzyl (2S,3R,5R)-3-(chloromethyl)-3-methyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate→(3,5-Dinitrophenyl)methyl (2S,3R,5R)-3-(chloromethyl)-3-methyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate→Benzyl (2S,3S,5R)-3-(azidomethyl)-3-methyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate→(3,5-Dinitrophenyl)methyl (2S,3S,5R)-3-(azidomethyl)-3-methyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate→Benzyl (2S,3S,5R)-3-(azidomethyl)-3-methyl-4,4,7-trioxo-4lambda6-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate→(3,5-Dinitrophenyl)methyl (2S,3S,5R)-3-(azidomethyl)-3-methyl-4,4,7-trioxo-4lambda6-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate→Acetylene→Benzyl (2S,3S,5R)-3-methyl-4,4,7-trioxo-3-[(1H-1,2,3-triazol-1-yl)methyl]-4lambda6-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate→(3,5-Dinitrophenyl)methyl (2S,3S,5R)-3-methyl-4,4,7-trioxo-3-[(1H-1,2,3-triazol-1-yl)methyl]-4lambda6-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate→(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

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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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