Synthesis of functional derivatives ofN-carboxamidomethyl- andN-phthalimidomethyl-a-amino acids and peptides by reaction of amides and nitriles of α-amino acids with formaldehyde and primary amides or phthalimide

Abstract

A direct method for the synthesis of functional derivatives ofN-carboxatnidomethyl- and N-phthalimidomethyl-a-amino acids by the reaction of nitriles and amides of α-amino acids (including peptides) with formaldehyde and NH-compounds (amides and imides) in DMF in the presence of TsOH was developed. The reactions of the compounds synthesized with acetic anhydride, tosyl chloride, and phcnylalanine benzylamide in the presence of dicyclohexylcarbodiimide affording the corresponding N-acyl and N-sulfonyl derivatives or peptides containing carboxamido- and phthalimidomethyl substituents at the terminal N-atom of the peptide chain, were studied.