GB786226A - Improvements in or relating to glutamic acid derivatives and process of making the same - Google Patents

Abstract

The invention comprises N-carboallyloxy-L-glutamic acids of the formula: <FORM:0786226/IV (b)/1> and N-carboallyloxy-L-glutamic acid anhydrides of the formula: <FORM:0786226/IV (b)/2> wherein R is hydrogen, phenyl or an alkyl group. The compounds are prepared by reacting L-glutamic acid with allylchloroformate, phenallylchloroformate or an alkylallyl chloroformate respectively, and, if desired, converting the resultant acid into its corresponding anhydride, e.g. by treatment with acetic anhydride, eThe reaction with L-glutamic acid is preferably carried out in the presence of a magnesium oxide catalyst. The N - carboallyloxy - L - glutamic acid anhydrides of the above formula may be treated with liquid ammonia to produce the corresponding N-carboallyloxy - L - glutamine. The latter compound may be subsequently converted to glutamine or a salt thereof by any one of the following methods: (1) by treatment with a hydrogen halide under anhydrous conditions, e.g. treatment with HCl or HBr in acetic acid; (2) by treatment with metallic sodium and liquid ammonia; and (3) by treatment with hydrogen in presence of a hydrogenation catalyst, e.g. Pt, Pd, Rh and Ni. The examples describe the preparation of L-glutamine, N-carboallyloxy-L - glutamic acid, N - carboallyloxy - L - glutamic anhydride, N-carboallyloxy-L-glutamine and the ammonium salt thereof. N-carbomethallyloxy - L - glutamic anhydride is also specified as a preferred compound.