CAS: 220031-86-7; 3-((2S,4S)-1-(Diisopropoxyphosphoryl)-4-Mercaptopyrrolidine-2-Carboxamido)Benzoic Acid

英文名称3-((2S,4S)-1-(Diisopropoxyphosphoryl)-4-Mercaptopyrrolidine-2-Carboxamido)Benzoic Acid
中文名称厄他培南杂质
IUPAC名称3-((2S,4S)-1-(diisopropoxyphosphoryl)-4-mercaptopyrrolidine-2-carboxamido)benzoic acid
其它别名Benzoic Acid, 3-[[[(2S,4S)-1-[bis(1-Methylethoxy)Phosphinyl]-4-Mercapto-2-Pyrrolidinyl]Carbonyl]Amino]-; 3-[[[(2S,4S)-1-[bis(1-Methylethoxy)Phosphinyl]-4-Mercapto-2-Pyrrolidinyl]Carbonyl]Amino]Benzoic Acid; Ertapenem Impurity Dipp
CAS编号220031-86-7
FDA UNII编号:4MM5LB8SFS
分子式:C18H27N2O6PS分子量:430.46
产品CID: 1141896
产品分类分析化学 → 标准品 → 药典标准品和杂质标准品

相似结构搜索
InChIKey: CKLWFRGLRHJOQP-HOTGVXAUSA-N
InChI=1S/C18H27N2O6PS/c1-11(2)25-27(24,26-12(3)4)20-10-15(28)9-16(20)17(21)19-14-7-5-6-13(8-14)18(22)23/h5-8,11-12,15-16,28H,9-10H2,1-4H3,(H,19,21)(H,22,23)/t15-,16-/m0/s
计算化学: 氢键受体数8.0氢键供体数3.0可旋转键数8.0

物理性质

LogP:2.3

MSDS等安全信息

上下游产品

meta-aminobenzoic acid (1S)-(3-oxo-2-thio-5-azabicyclo[2.2.1]hept-5-yl)phosphonic acid bis(1-methylethyl) ester N‐(O,O‐diisopropylphosphoryl)-trans-4‐hydroxy-L-proline (2S-trans)-1-[bis(1-methylethoxy)phosphinyl]tetrahydro-4-hydroxy-2H-pyrrole-2-carboxylic acid diphenylphosphinyl ester (2S-cis)-3-[[(4-mercapto-2-pyrrolidinyl)carbonyl]amino]benzoic acid monohydr°Chloride (2S)-cis-3-[[(4-mercapto-2-pyrrolidinyl)carbonyl]amino]benzoic acid monohydr°Chloride disulfide

合成工艺路线路线简述

📜(2S-Trans)-1-[bis(1-Methylethoxy)Phosphinyl]Tetrahydro-4-Hydroxy-2H-Pyrrole-2-Carboxylic Acid Diphenylphosphinyl Ester置于吡啶,Sodium Sulfide体系中,用二氯甲烷,水,溶剂黄146 用作溶剂,化学反应 2.61H,反应生成厄他培南杂质
参考文献:Efficient One-Pot Synthesis Of The 2-Aminocarbonylpyrrolidin-4-Ylthio-Containing Side Chain Of The New Broad-Spectrum Carbapenem Antibiotic Ertapenem
标题:Efficient One-Pot Synthesis Of The 2-Aminocarbonylpyrrolidin-4-Ylthio-Containing Side Chain Of The New Broad-Spectrum Carbapenem Antibiotic Ertapenem
摘要:An Efficient Synthesis Of The 2-Aminocarbonylpyrrolidin-4-Ylthio Containing Side Chain Of Ertapenem (Mk-0826) Is Described. Starting Material N-(O,O-Diisopropyl Phosphoryl)-Trans-4-Hydroxy-L-Proline Is Converted In A One-Pot Process To (2S)-Cis-3-[[(4-Mercapto-2-Pyrrolidinyl)Carbonyl] Amino] Benzoic Acid Monohydrochloride In 70-75% Overall Yield Via A Series Of Six Reactions. The Development Of Each Of These Reactions And The Isolation Of The Product Is Discussed In Detail.
Doi:10.1021/jo011170C