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Synthesis of N-(1-carboxy-3-phenylpropen-2yl)alanylproline
Authors:V A Slavinskaya  G I Chipens  M Yu Katkevich  D É Sile  É Kh Korchagova  V D Grigor'eva  É Lukevits
Institution:(1) Latvian Institute of Organic Chemistry, LV-10-06 Riga
Abstract:A method has been developed for the synthesis of N-(1-carboxy-3-phenylpropen-2-yl)atanylproline by reductive alkylation of alanylproline by the sodium salt of 2-oxo-4-phenylbutenoic acid, using sodium cyanoborohydride and sodium borchydride as reducing agents. The products were separated chromatographically. Under the conditions of the reaction, sodium borohydride in a neutral medium preferentially reduces the double bond of the Schiff base. Sodium cyanoborohydride reduces, in addition, the double bond of the 2-oxo-4-phenylbutenoic acid, forming enalaprilate.Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 4, pp. 468–471, April, 1996.
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