FIELD: chemistry.
SUBSTANCE: invention relates to a method of producing (2S,4S)-3-(3-acetylthiopropionyl)-6-oxohexahydropyrimidine-4-carboxylic acid derivatives - potential anti-hypertensive agents, angiotensin converting enzyme inhibitors. The method involves obtaining a Na-salt of optically pure (2S,4S)-2-alkyl-6-oxohexahydropyrimidine-4-carboxylic acid by reacting natural amino acid L-asparagine with a series of aliphatic, aromatic or fatty-aromatic aldehydes containing 4-8 carbon atoms in aqueous or aqueous-methanol solution at pH 9-11 at room temperature, wherein the ratio of components during reaction is selected from 1:1 to 1:1.5 mol %, followed by adding an acid chloride of 3-acetylmercaptopropionic acid in amount of 1.1-1.5 mol % of the weight of the components directly into the reaction mixture after formation of (2S,4S)-2-alkyl-6-oxohexahydropyrimidine-4-carboxylic acid.
EFFECT: end product obtained using the disclosed method is optically pure and is produced using natural or commercially available compounds.
1 cl, 7 ex
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Authors
Dates
2012-07-10—Published
2011-03-22—Filed