77328-17-7Relevant academic research and scientific papers
Synthesis of Strombine. A New Method for Monocarboxymethylation of Primary Amines
Kihlberg, Jan,Bergman, Rolf,Wickberg, Boerje
, p. 911 - 916 (2007/10/02)
Many common methods for monocarboxymethylation of primary amines give various amounts of dialkylated by-products.In this work the reaction of two equivalents of glyoxilic 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)-N-formyl derivative of the amine under mild conditions in carboxylic acid solvents.Hydrolysis then produces the monocarboxymethylated primary amine in good to exellent overall yield.Proof that the intermediate product is not obtained via the Leuckart reaction is given.
