A Facile Synthesis of 2-Aminopropane-1,2,3-tricarboxylic Acid and Its Symmetrical Dimethyl Ester

A new convenient synthetic route to 2-aminopropane-1,2,3-tricarboxylic acid is described. The first two stages of the three-step synthesis are performed in a one-pot procedure and include the cyclization of hippuric acid with DCC followed by treatment with methyl bromoacetate to yield an alkylated oxazolone. Its hydrolysis with HCl provides 2-aminopropane-1,2,3-tricarboxylic acid as its HCl salt. Esterification of the resulting acid with methanol in the presence of thionyl chloride leads selectively to its symmetrical diester.

Automated summary

A new convenient synthetic route for 2-aminopropane-1,2,3-tricarboxylic acid is described, involving two initial steps conducted in a one-pot procedure. The successful synthesis is achieved through the cyclization of hippuric acid and subsequent hydrolysis with HCl.