SYNTHESIS OF AMINO ACIDS FROM SUBSTITUTED CYANOACETIC ESTERS

Nine α-amino acids, namely, dl-α-aminoundecylic acid, dl-α-aminostearic acid, dl-α-amino-β-methylcaproic acid, dl-α-amino-β-ethylvaleric acid, dl-α-amino-β-methylenanthic acid, dl-α-amino-α-acetylacetic acid, dl-α-amino-γ-cyclohexylbutyric acid, dl-α-(1-indanyl)-α-aminoacetic acid, and dl-proline have been prepared from ethyl alkylcyanoacetates. When a mixture of formic and hydrochloric acids and water was used, instead of hydrochloric acid, as hydrolyzing agent, α-amino-β-ethylvaleric acid and α-(1-indanyl)-α-aminoacetic acid were obtained with better yields. The following compounds, as far as the authors are aware, have been prepared for the first time: ethyl α-cyanoundecylate, α-cyanoundecylic hydrazide, anisal α-cyanoundecylic hydrazide, α-cyanoundecylic azide, α-carbethoxyaminoundecylonitrile, dl-α-aminoundecylic acid, 5-(n-nonyl)-hydantoin, α-cyanostearic hydrazide, anisal α-cyanostearic hydrazide, α-cyanostearic azide, α-carbethoxyaminostearonitrile, α-cyano-β-methylcaproic hydrazide, anisal α-cyano-β-methylcaproic hydrazide, α-cyano-β-methylcaproic azide, α-carbethoxyamino-β-methylcaproonitrile, dl-α-amino-β-methylcaproic acid and its copper salt, α-cyano-β-ethylvaleric hydrazide, anisal α-cyano-β-ethylvaleric hydrazide, α-cyano-β-ethylvaleric azide, α-carbethoxyamino-β-ethylvaleronitrile, dl-α-amino-β-ethylvaleric acid, and its copper salt, ethyl α-cyano-β-methylenanthate, α-cyano-β-methylenanthic hydrazide, anisal α-cyano-β-methylenanthic hydrazide, α-cyano-β-methylenanthic azide, α-carbethoxyamino-β-methylenanthonitrile, dl-α-amino-β-methylenanthic acid, and its copper salt, α-cyano-α-acetylacetic hydrazone, anisal α-cyano-α-acetylacetic hydrazone, α-cyano-α-acetylacetic azide, α-carbethoxyamino-α-acetylacetonitrile, dl-α-amino-α-acetylacetic acid, ethyl-α-cyano-γ-cyclohexylbutyrate, α-cyano-γ-cyclohexylbutyric hydrazide, anisal α-cyano-γ-cyclohexylbutyric hydrazide, α-cyano-γ-cyclohexylbutyric azide, α-carbethoxyamino-γ-cyclohexylbutyronitrile, 5-(β-cyclohexylethyl)-hydantoin, 1-in-danyl bromide, ethyl α-(1-indanyl)-α-cyanoacetate, α-(1-indanyl)-α-cyanoacetic hydrazide, anisal α-(1-indanyl)-α-cyanoacetic hydrazide, α-(1-indanyl)-α-cyanoacetic azide, α-(1-indanyl)-α-carbethoxyaminoacetonitrile, dl-α-(1-indanyl)-α-aminoacetic acid, and its copper salt, ethyl δ-chloro-α-cyanovalerate, δ-chloro-α-cyanovaleric hydrazide, anisal δ-chloro-α-cyanovaleric hydrazide, δ-chloro-α-cyanovaleric azide, δ-chloro-α-carbethoxyaminovaleronitrile.