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Synthesis of amino acids from substituted cyanoacetic esters

, : Synthesis of amino acids from substituted cyanoacetic esters. Canadian Journal of Research 26(7): 503-510

Nine alpha-amino acids were prepared in the racemic form from the alpha-substituted cyanoacetic esters, namely, alanine, alpha-amino-butyric acid, alpha-aminoenanthic acid, alpha-amino-gamma-phenoxybutyric acid, phenyl-glycine, proline, ornithine, lysine and 2-aminoindane-2-carboxylic acid. Pyrrolidine or piperidine was isolated when it was attempted to prepare ornithine or lysine by hydrolysis of diurethanes with HCl. When a mixture of formic acid, water and HC1 was used as hydrolyzing agent, ornithine or lysine was obtained in low yield in addition to traces of pyrrolidine or piperidine. Some 40 intermediate compounds, as far as the authors are aware, were prepared for the first time.


PMID: 18875064

DOI: 10.1139/cjr48b-051

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