Synthesis of N-Z, N-Formyl alpha-Amino Acid Derived Gem-Diamines

摘要

A variety of N-carbobenzoxy, N-formyl gem-diaminoalkyl derivatives have been obtained through Goldsmith-Wick reaction of Z-alpha-amino acid/peptide acid derived isocyanates with 96% HCOOH in presence of 4-dimethylaminopyridine (DMAP) as catalyst. The reaction proceeds to completion within 2-4 h and results in good yields of the products isolated as stable solids.Formamides are medicinally and synthetically useful class of compounds. They form precursors for the preparation of wide range of important organic compounds like form-amidines, monomethylated amines, nitrogen containing hetrocycles and in Vielsmier formylation reactions. As catalysts, they are employed in asymmetric allylations and hydrosilylation of carbonyl compounds. N-Formyl amino acid esters are employed in enzymatic synthesis of peptides in aqueous media.