Bifunctional chelating agents. Part 2. Synthesis of 1-(2-carboxyethyl)ethylenediaminetetra-acetic acid by ring cleavage of a substituted imidazole

Abstract

The synthesis of 1-(2-carboxyethyl)ethylenediaminetetra-acetic acid, a new bifunctional analogue of ethylenediaminetetra-acetic acid (EDTA) is described. This is carried out via ring-opening benzoylation of ethyl imidazol-4-ylpropanoate, hydrogenation and hydrolysis to 4,5-diaminovaleric acid (DL-γ-ornithine) dihydrochloride, and subsequent alkylation.