合成路线:D-Serine (I) is nitrosated in the presence of bromide ion to give (R)-2-bromo-3-hydroxypropanoic acid (II),which is converted into (R)-2-hydroxy-3-(methylthio)propanoic acid (IV),via the epoxy acid (III),using sodium methoxide followed by sodium methanethiolate.This hydroxy acid (IV) is coupled to (S)-3-(acetylthio)-2-methylpropanoic acid using either the imidazolide or acid chloride.Final deprotection of 2(R)-[3-(acetylthio)-2(S)-methyl-1-oxopropoxy]-3-(methylthio)propanoic acid (V) is achieved using aqueous ammonia.FPL 66564 is conveniently isolated either as the 1-adamantanamine or L-lysine salt.
参考文献标题:FPL 66564,the first ultra short-acting angiotensin converting enzyme inhibitor (USACEI)
文献作者:Baxter,A.J.G.; Hallam,C.; Harper,S.T.; Meghani,P.
参考来源:J Hypertension 1992,10(Suppl.4),S147
合成路线:D-Serine (I) is nitrosated in the presence of bromide ion to give (R)-2-bromo-3-hydroxypropanoic acid (II),which is converted into (R)-2-hydroxy-3-(methylthio)propanoic acid (IV),via the epoxy acid (III),using sodium methoxide followed by sodium methanethiolate.This hydroxy acid (IV) is coupled to (S)-3-(acetylthio)-2-methylpropanoic acid using either the imidazolide or acid chloride.Final deprotection of 2(R)-[3-(acetylthio)-2(S)-methyl-1-oxopropoxy]-3-(methylthio)propanoic acid (V) is achieved using aqueous ammonia.FPL 66564 is conveniently isolated either as the 1-adamantanamine or L-lysine salt.
参考文献标题:FPL 66564
文献作者:Carr,R.D.; Baxter,A.J.G.
参考来源:Drugs Fut 1993,18(1),12
合成路线:D-Serine (I) is nitrosated in the presence of bromide ion to give (R)-2-bromo-3-hydroxypropanoic acid (II),which is converted into (R)-2-hydroxy-3-(methylthio)propanoic acid (IV),via the epoxy acid (III),using sodium methoxide followed by sodium methanethiolate.This hydroxy acid (IV) is coupled to (S)-3-(acetylthio)-2-methylpropanoic acid using either the imidazolide or acid chloride.Final deprotection of 2(R)-[3-(acetylthio)-2(S)-methyl-1-oxopropoxy]-3-(methylthio)propanoic acid (V) is achieved using aqueous ammonia.FPL 66564 is conveniently isolated either as the 1-adamantanamine or L-lysine salt.
参考文献标题:(R)-2-(3-Mercapto-2(S)-methyl-1-oxopropoxy)-3-(methylthio)propanoic acid (FPL 66564),the first ultra short-acting angiotensin converting enzyme inhibitor (USACEI)
文献作者:Baxter,A.J.G.; Carr,R.D.; Eyley,S.C.; Fraser-Rae,L.; Hallam,C.; Harper,S.T.; Hurved,P.A.; King,S.J.; Meghani,P.
参考来源:J Med Chem 1992,353718-20
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