Many common methods for monocarboxymethylation of primary amines give various amounts of dialkylated by-products. In this work the reaction of two equivalents of glyoxylic acid with representative primary aliphatic and aromatic amines, as well as with amino acids and a dipeptide, is shown to give only the N-(carboxymethyl)-iV*-formyl derivative of the amine under mild conditions in carboxylic acid solvents. Hydrolysis then produces the ...
[Borecka-Bednarz, Bozena; Bree, Alan V.; Patrick, Brian O.; Scheffer, John R.; Trotter, James Canadian Journal of Chemistry, 1998 , vol. 76, # 11 p. 1616 - 1632]