Synthesis of N-(1-carboxy-3-phenylpropen-2yl)alanylproline

descriptionPublicationkeyboard_double_arrow_right Article 01 Apr 1996 English Publisher:Springer Science and Business Media LLCJournal:Chemistry of Heterocyclic Compounds, volume 32, pages 405-407 (issn: 0009-3122, eissn: 1573-8353,

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Authors: V. A. Slavinskaya; G. I. Chipens; M. Yu. Katkevich; D. �. Sile; �. Kh. Korchagova; V. D. Grigor'eva; �. Lukevits;

doi: 10.1007/bf01165900

Synthesis of N-(1-carboxy-3-phenylpropen-2yl)alanylproline

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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.

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Institute of Organic Chemistry
Hungary

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