The title compound (with the systematic name 2-{[(1S)-1-(methoxycarbonyl)-3-methylbutyl]aminocarbonyl}benzoic acid), C15H19NO5, crystallizes in the monoclinic space group P2(1), with two independent molecules per asymmetric unit. The most notable difference between the two molecules is in the dihedral angles between the planes of the carboxyl group and the benzene ring, which are 3.5 (3) and 25.7 (1) degrees . This difference may account for the fact that two competing reactions are observed in aqueous solution, namely cyclization to form the imide N-phthaloylleucine and hydrolysis of N-(2-carboxybenzoyl)-L-leucine methyl ester to phthalic acid and leucine.
A Convenient Synthesis of Optically Active N-(o-Carboxybenzoyl)-L-amino Acids.-Modified procedures are given for the synthesis of compounds (V) and (VI) in high optical purities. Compounds of type (VI) can also be prepared by reacting (I) with phthalic anhydride (IV). The compounds are useful as simple models of aspartic proteinases [for intermediates (III) no yields given]. -(ONOFRIO, ALVARO B.; JOUSSEF, ANTONIO C.; NOME, FARUK; Synth. Commun. 29 (1999) 17, 3039-3049; Dep. Quim., Univ. Fed.
scite is a Brooklyn-based organization that helps researchers better discover and understand research articles through Smart Citations–citations that display the context of the citation and describe whether the article provides supporting or contrasting evidence. scite is used by students and researchers from around the world and is funded in part by the National Science Foundation and the National Institute on Drug Abuse of the National Institutes of Health.