Pivalopril, Pivopril, USV 3659(S), RHC 3659(S), REV 3659(S)
匹伏普利Chemical Name: (-)-(S)-N-Cyclopentyl-N-[3-(2,2-dimethyl-1-oxopropyl)thio]-2-methyl-1-oxopropyl]glycine
CAS No. 81045-50-3
项目整合开发状态: Clinical
项目研究机构: Revlon (Originator)
合成路线:The reaction of cyclopentylamine (I) with tertbutyl bromoacetate (II) by means of NH3 in acetonitrile gives N-cyclopentylglycine tert-butyl ester (III),which is condensed with 3-(acetylthio)-2-methylpropionyl chloride (IV) [prepared from the corresponding acid (V) with SOCl2] by means of triethylamine in dioxane to yield the acylated glycine (VI).Deacetylation of (VI) with dry ammonia in methanol affords the mercapto derivative (VII),which is acylated with pivaloyl chloride (VIII) in the usual way giving the corresponding thio ester (IX).Finally,this compound is hydrolyzed partially with trimethylsilyl iodide in methylene chloride.
📌 参考资料/链接：
参考文献标题:Pivopril
文献作者:Castar,J.; Serradell,M.N.
参考来源:Drugs Fut 1986,11(2),116
📄 详细内容
合成路线:The reaction of cyclopentylamine (I) with tertbutyl bromoacetate (II) by means of NH3 in acetonitrile gives N-cyclopentylglycine tert-butyl ester (III),which is condensed with 3-(acetylthio)-2-methylpropionyl chloride (IV) [prepared from the corresponding acid (V) with SOCl2] by means of triethylamine in dioxane to yield the acylated glycine (VI).Deacetylation of (VI) with dry ammonia in methanol affords the mercapto derivative (VII),which is acylated with pivaloyl chloride (VIII) in the usual way giving the corresponding thio ester (IX).Finally,this compound is hydrolyzed partially with trimethylsilyl iodide in methylene chloride.
参考文献标题:Angiotensin-converting enzyme inhibitors.New orraly active antihypertensive (mercaptoalkanoyl)- and [(acylthio)alkanoyl]glycine derivatives
文献作者:Suh,J.T.; Skiles,J.W.; Williams,B.E.; Youssefyeh,R.D.; Jones,H.; Loev,B.; Neiss,E.S.; Schwab,A.; Mann,W.S.; Khandwala,A.; et al.
参考来源:J Med Chem 1985,28(1),57-66
产品链接: CAS No. 81045-50-3››