GB728970A - Improvements in process for the production of aminocarboxylic acids and their n-substituted derivatives - Google Patents

Abstract

Amino carboxylic acids and their N-substituted derivatives in which a hydrogen of the amino group is substituted by an acyl group are produced by reacting lactones of the formula <FORM:0728970/IV (b)/1> (in which R1 is a substituted or unsubstituted carbon chain and X is hydrogen or an alkyl radical) with carboxylic acid amides at elevated temperatures, advantageously with the exclusion of moisture, to give N-substituted aminocarboxylic acids which may be saponified with mineral acids or alkali solutions to give amino carboxylic acids. Lactones containing acylatable groups may be used as starting materials, the acylatable groups being unaffected by the reaction. Alternatively when amino carboxylic acids are required as end products lactones which are substituted by groups which can react with ammonia may be used, e.g. if a lactone substituted by halogen is used an aminocarboxylic acid which still contains halogen is obtained. The lactones may be reacted with aliphatic, aromatic, alicyclic or heterocyclic acid amides, e.g. formamide, acetamide, propionamide, benzoylamide and the amides of palmitic, stearic and salicylic acids. In the examples (a) a -amino-g -butyrolactone is reacted with formamide to give the compound of formula H.OC.NH.CH2CH2CHNH2COOH, which is hydrolysed with hydrochloric acid to give the hydrochloride of a -g -diamino butyric acid; and (b) a -bromo-g -butyrolactone is heated with formamide to give <FORM:0728970/IV (b)/2> which is hydrolysed with hydrochloric acid to give the hydrochloride of a -bromo-g -aminobutyric acid.