化学
氯化亚砜
卡托普利
光学活性
脯氨酸
氯化物
药物化学
立体化学
有机化学
氨基酸
生物化学
医学
血压
放射科
作者
Masami Shimazaki,Junzo Hasegawa,Kazunori Kan,Kenji Nomura,Yasushi Nose,Hideo Kondo,Takeki Ohashi,Kiyoshi Watanabe
出处
期刊:Chemical & Pharmaceutical Bulletin
[Pharmaceutical Society of Japan]
日期:1982-01-01
卷期号:30 (9): 3139-3146
被引量:49
摘要
A synthesis of N-(3-mercapto-2-D-methylpropanoyl)-L-proline (1, Captopril) is described in which the key intermediate, optically active 3-chloro-2-D-methylpropanoyl chloride (3b), was prepared by treating microbiologically derived optically active 3-hydroxy-2-D-methylpropanoic acid (2) with thionyl chloride. The compound 3b was coupled with L-proline to afford the chloride (4) which was directly converted into Captopril by reaction with hydrosulfide or trithiocarbonate ion in hot water with retention of the stereochemistry. The preparation of another useful intermediate, 3-acetylthio-2-D-methylpropanoic acid (9a), is also described.
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