Synthesis ofN-(amidomethyl)- andN- (imidomethyl)-α-amino acid esters by reactions of α-amino acid esters with formaldehyde and amides or imides

摘要

Reactions of hydrochlorides of glycine, alanine, phenylalanine, L-isolcucinc, and L-valine esters with aromatic and heteroaromatic carboxamides afforded hydrochlorides of the correspondingN-(amidomethyl)-α-amino acid esters.N-(Phthalimidomethyl)-α-amino acid esters were obtained by reactions of α-amino acid esters containing free amino groups with formaldehyde and phthalimide, The1H NMR studies demonstrated that the chiral centers of α-amino acids may be retained in the course of condensation. Reactions of the Mannish bases obtained and their hydrochlorides with acetic anhydride and tosyl chloride afforded the correspondingN-aryl andN-sulfonyl derivati