Acta Chem Scand

Synthesis of strombine: a new method for monocarboxymethylation of primary amines

J Kihlberg, R Bergman, B Wickberg

Index: Kihlberg, Jan; Bergman, Rolf; Wickberg, Boerje Acta Chemica Scandinavica, Series B: Organic Chemistry and Biochemistry, 1983 , vol. 37, # 10 p. 911 - 916

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Citation Number: 12

Abstract

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 ...