SYNTHESIS OF N-(AMIDOMETHYL)-ALPHA-AMINO AND N-(IMIDOMETHYL)-ALPHA-AMINO ACID-ESTERS BY REACTIONS OF ALPHA-AMINO-ACID ESTERS WITH FORMALDEHYDE AND AMIDES OR IMIDES

Reactions of hydrochlorides of glycine, alanine, phenylalanine, L-isol eucine, and L-valine esters with aromatic and heteroaromatic carboxami des afforded hydrochlorides of the corresponding N-(amidomethyl)-alpha -amino acid esters. N-(Phthalimidomethyl)-alpha-amino acid esters were obtained by reactions of alpha-amino acid esters containing free amin o groups with formaldehyde and phthalimide. The H-1 NMR studies demons trated that the chiral centers of alpha-amino acids may be retained in the course of condensation. Reactions of the Mannich bases obtained a nd their hydrochlorides with acetic anhydride and tosyl chloride affor ded the corresponding N-acyl and N-sulfonyl derivatives.