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

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Chemistry of Heterocyclic Compounds Aims and scope

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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Authors and Affiliations

  1. Latvian Institute of Organic Chemistry, LV-10-06, Riga

    V. A. Slavinskaya, G. I. Chipens, M. Yu. Katkevich, D. É. Sile, É. Kh. Korchagova, V. D. Grigor'eva & É. Lukevits

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  1. V. A. Slavinskaya
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  2. G. I. Chipens
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  3. M. Yu. Katkevich
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  4. D. É. Sile
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  5. É. Kh. Korchagova
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  6. V. D. Grigor'eva
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  7. É. Lukevits
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Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 4, pp. 468–471, April, 1996.

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Slavinskaya, V.A., Chipens, G.I., Katkevich, M.Y. et al. Synthesis of N-(1-carboxy-3-phenylpropen-2yl)alanylproline. Chem Heterocycl Compd 32, 405–407 (1996). https://doi.org/10.1007/BF01165900

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  • DOI: https://doi.org/10.1007/BF01165900

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