Synthesis of Strombine. A New Method for Monocarboxymethylation of Primary Amines.

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Abstract
Many common methods for monocarboxymethylation of primary amines give various amounts of dialkylated by-products. The reaction of 2 equivalents of glyoxylic acid with representative primary aliphatic and aromatic amines, as well as with amino acids and a dipeptide, gives 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 excellent overall yield. Proof that the intermediate product is not obtained via the Leuckart reaction is given.

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