SYNTHESIS OF AMINO ACIDS FROM SUBSTITUTED CYANOACETIC ESTERS

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Abstract
Nine α-amino acids, namely, dl-alanine, dl-α-aminobutyric acid, dl-α-ammoenanthic acid, dl-α-amino-γ-phenoxybutyric acid, dl-C-phenylglycine, dl-proline, dl-ornithine, dl-lysine and 2-aminoindane-2-carboxylic acid have been prepared from α-substituted cyanoacetic esters. Pyrrolidine or piperidine was isolated when it was attempted to prepare ornithine or lysine by hydrolysis of diurethanes with hydrochloric acid. When a mixture of formic and hydrochloric acids and water was used as hydrolyzing agent, ornithine or lysine was obtained in low yield in addition to traces of pyrrolidine or piperidine. The following compounds, as far as the authors are aware, have been prepared for the first time: α-cyanopropionhydrazide, benzal α-cyanopropionhydrazide, α-cyanopropionic azide, α-carbethoxyaminopropiononitrile, α-cyanobutyrhydrazide, benzal α-cyanobutyrhydrazide, α-cyanobutyric azide, α-carbethoxyaminobutyronitrile, ethyl α-cyanoenanthate, α-cyanoenanthic hydrazide, benzal α-cyanoenanthic hydrazide, α-cyanoenanthic azide, α-carbethoxyaminoenanthonitrile, 5-(n-amyl)-hydantoin, ethyl α-cyano-γ-phenoxybutyrate, ethyl bis-β-phenoxyethylmalonate mononitrile, α-cyano-γ-phenoxybutyrhydrazide, benzal α-cyano-γ-phenoxybutyrhydrazide, α-cyano-γ-phenoxybutyric azide, α-carbethoxyamino-γ-phenoxybutyronitrile, 5-(β-phenoxyethyl)-hydantoin, α-cyano-α-phenylacethydrazide, benzal α-cyano-α-phenylacethydrazide, α-cyano-α-phenylacetic azide, ethyl δ-bromo-α-cyanovalerate, δ-bromo-α-cyanovalerhydrazide, benzal δ-bromo-α-cyanovalerhydrazide, δ-bromo-α-cyanovaleric azide, δ-bromo-α-carbethoxyaminovaleronitrile, dibenzal α-cyanoadipic dihydrazide, α-cyanoadipic diazide, α,δ-dicarbethoxyaminoadiponitrile, dibenzal α-cyanopimelic dihydrazide, α-cyanopimelic diazide, α, ε-dicarbethoxyaminocapronitrile, 2-cyano-2-carbethoxyindane, 2-cyano-2-carboxylindane hydrazide, benzal 2-cyano-2-carboxylindane hydrazide, 2-cyano-2-carboxylindane azide, 2-cyano-2-carbethoxyaminoindane, 2-aminoindane-2-carboxylic acid, 2-aminoindane-2-carboxylic acid hydrochloride.

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