(Z)-7-chloro-2-({[(1S)-2,2-dimethylcyclopropyl]carbonyl}amino)-2-heptenoic acid -Drug Synthesis Database

【结构式】

【分子编号】61848

【品名】(Z)-7-chloro-2-({[(1S)-2,2-dimethylcyclopropyl]carbonyl}amino)-2-heptenoic acid

【CA登记号】

【分子式】C₁₃H₂₀ClNO₃

【分子量】273.75944

【元素组成】C 57.04% H 7.36% Cl 12.95% N 5.12% O 17.53%

与该中间体有关的原料药合成路线共 1 条

合成路线1

该中间体在本合成路线中的序号：(IV)

The condensation of 7-chloro-2-oxoheptanoic acid ethyl ester (I) with (S)-2,2-dimethylcyclopropanecarboxamide (II) by means of TsOH in refluxing toluene gives (S)-7-chloro-2-(2,2-dimethylcyclopropanecarboxamido)-2-heptenoic acid ethyl ester (III), which is hydrolyzed in aq. NaOH to yield the corresponding carboxylic acid (IV). Finally, this compound is condensed with (R)-cysteine (V) by means of NaOH in water to afford the target Cilastatino.

参考文献中间体

合成目标

【1】 Tyagi, O.D.; Kumar, Y.; Srivastava, T.K. (Ranbaxy Laboratories Ltd.); Process for the preparation of cilastatin. WO 03018544 .

中间体序号	中间体编号	品名	CAS号	分子式	供应商	用于合成
(I)	61845	propyl 7-chloro-2-oxoheptanoate		C₁₀H₁₇ClO₃	详情	详情
(II)	61846	(1S)-2,2-dimethylcyclopropanecarboxamide		C₆H₁₁NO	详情	详情
(III)	61847	propyl (Z)-7-chloro-2-({[(1S)-2,2-dimethylcyclopropyl]carbonyl}amino)-2-heptenoate		C₁₆H₂₆ClNO₃	详情	详情
(IV)	61848	(Z)-7-chloro-2-({[(1S)-2,2-dimethylcyclopropyl]carbonyl}amino)-2-heptenoic acid		C₁₃H₂₀ClNO₃	详情	详情
(V)	14643	L-cysteine; (R)-2-Amino-3-mercaptopropionic acid	52-90-4	C₃H₇NO₂S	详情	详情

Extended Information