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CAS 125949-72-6

(2S,3S,5R)-2-Methyl-2-(1H-1,2,3-triazol-1-ylmethyl)penam-3-carboxylic acid diphenylmethyl ester

登记编号:Tazobactam Sodium-020

应用背景(按来源药适应症)

腹腔感染他唑巴坦钠/头孢洛生呼吸机相关性肺炎他唑巴坦钠/头孢洛生泌尿系统感染他唑巴坦钠/头孢洛生社区获得性细菌肺炎他唑巴坦钠/头孢洛生肾盂肾炎他唑巴坦钠/头孢洛生医院获得性肺炎他唑巴坦钠/头孢洛生细菌感染头孢他啶/他唑巴坦钠呼吸道感染头孢他啶/他唑巴坦钠泌尿系统感染头孢他啶/他唑巴坦钠

来源药(使用该中间体的合成路线)

品种梯队到期年
他唑巴坦钠/头孢洛生Tazobactam Sodium/CeftolozaneTier C · 观察 / 贸易-
头孢他啶/他唑巴坦钠Ceftazidime/Tazobactam SodiumTier C · 观察 / 贸易-

合成路线中的位置(上下游链)

按路线登记顺序排列,左→右为合成方向;高亮为当前 CAS,其余可点击跳转对应档案。

他唑巴坦钠/头孢洛生工艺路线步数:7总收率:1046.36g(Tazobactam Sodium-009)
(2S-(2alpha,3beta,5alpha))-3-(Chloromethyl)-3-methyl-7-oxo-4-thia-1-azabicyclo(3.2.0)heptane-2-carboxylic acid diphenylmethyl ester→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→Ethanedial→Diamine→1,1'-(Ethane-1,2-diylidene)dihydrazine→1H-1,2,3-Triazol-1-amine→3-Amino-1-([(2S,3S,5R)-2-[(diphenylmethoxy)carbonyl]-3-methyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptan-3-yl]methyl)-1H-1,2,3-triazol-3-ium chloride→3-Amino-1-([(2S,3S,5R)-2-[(diphenylmethoxy)carbonyl]-3-methyl-4,4,7-trioxo-4lambda6-thia-1-azabicyclo[3.2.0]heptan-3-yl]methyl)-1H-1,2,3-triazol-3-ium chloride→2-Propynoic acid→(2S,3S,5R)-2-Methyl-2-(1H-1,2,3-triazol-1-ylmethyl)penam-3-carboxylic acid diphenylmethyl ester
他唑巴坦钠/头孢洛生优化路线步数:14总收率:17g(Tazobactam Sodium-029)
(+)-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
他唑巴坦钠/头孢洛生优化路线步数:7总收率:5g(Tazobactam (Free))
1,2,3-Triazole→Silver(1+) 1,2,3-triazol-1-ide→(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→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→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→Diphenylmethyl (2S,3R,5R)-3-(bromomethyl)-3-methyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate→Diphenylmethyl (2S,3R,4R,5R)-3-(bromomethyl)-3-methyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate 4-oxide→(Z)-Ethene-1,2-diamine hydrogen chloride→Diphenylmethyl (2S,3S,4R,5R)-3-methyl-7-oxo-3-(1H-1,2,3-triazol-1-ylmethyl)-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate 4-oxide
头孢他啶/他唑巴坦钠工艺路线步数:7总收率:1046.36g(Tazobactam Sodium-009)
(2S-(2alpha,3beta,5alpha))-3-(Chloromethyl)-3-methyl-7-oxo-4-thia-1-azabicyclo(3.2.0)heptane-2-carboxylic acid diphenylmethyl ester→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→Ethanedial→Diamine→1,1'-(Ethane-1,2-diylidene)dihydrazine→1H-1,2,3-Triazol-1-amine→3-Amino-1-([(2S,3S,5R)-2-[(diphenylmethoxy)carbonyl]-3-methyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptan-3-yl]methyl)-1H-1,2,3-triazol-3-ium chloride→3-Amino-1-([(2S,3S,5R)-2-[(diphenylmethoxy)carbonyl]-3-methyl-4,4,7-trioxo-4lambda6-thia-1-azabicyclo[3.2.0]heptan-3-yl]methyl)-1H-1,2,3-triazol-3-ium chloride→2-Propynoic acid→(2S,3S,5R)-2-Methyl-2-(1H-1,2,3-triazol-1-ylmethyl)penam-3-carboxylic acid diphenylmethyl ester
头孢他啶/他唑巴坦钠优化路线步数:14总收率:17g(Tazobactam Sodium-029)
(+)-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
头孢他啶/他唑巴坦钠优化路线步数:7总收率:5g(Tazobactam (Free))
1,2,3-Triazole→Silver(1+) 1,2,3-triazol-1-ide→(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→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→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→Diphenylmethyl (2S,3R,5R)-3-(bromomethyl)-3-methyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate→Diphenylmethyl (2S,3R,4R,5R)-3-(bromomethyl)-3-methyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate 4-oxide→(Z)-Ethene-1,2-diamine hydrogen chloride→Diphenylmethyl (2S,3S,4R,5R)-3-methyl-7-oxo-3-(1H-1,2,3-triazol-1-ylmethyl)-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate 4-oxide

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