Captopril, SQ-14225, Captril, Cesplon, Tensiomin, Capoten

卡托普利Chemical Name: 1-[(2S)-3-Mercapto-2-methyl-1-oxopropyl]-L-proline; N-[(2S)-3-Mercapto-2-methylpropionyl]-L-proline
CAS No. 62571-86-2
项目整合开发状态: Launched-1980
项目研究机构: Bristol-Myers Squibb (Originator), Sankyo (Not Determined), Egis (Licensee), Esteve (Licensee)
合成路线:It is prepared by hydrolysis with ammonia in methanol of N-(3-acetylthio-2-methylpropanoyl)-L-proline (I).Compound (I) can be obtained in three different ways:1) The reaction of L-proline tert-butyl ester (II) with 3-acetylthio-2-methyl-propanoic acid (III) by means of dicyclohexylcarbodiimide in CH2Cl2 gives N-(3-acetylthio-2-methylpropanoyl)-L-proline tert-butyl ester (IV),which is hydrolyzed with trifluoroacetic acid in anisole.2) By condensation of L-proline (V) with 3-acetylthio-2-methylpropanoyl chloride (VI) (prepared from the corresponding acid (III) with SOCl2) by means of NaOH in water.3) The condensation of L-proline (V) with methacryloyl chloride (VII) by means of NaHCO3 in water yields N-methacryloyl-L-proline (VIII),which is then treated with thiolacetic acid (A) and azobisisobutyronitrile.The acid (III) is obtained by addition of thiolacetic acid (IX) to methacrylic acid (X) at 100 C.