SYNTHESIS OF THE POTENTIAL DIPEPTIDE NEUROLEPTIC DILEPT AND ITS ACTIVE METABOLITE

摘要

The new potential neuroleptic drug dilept (N-caproyl-I-prolyl-L-tyrosine methyl ester) was created. A four-step scalable synthetic method for dilept that enabled the product to be obtained in 52% yield without racemization was presented. The process included preparation of caproic acid chloride using thionylchloride, Schotten-Baumann acylation of L-proline by the obtained acid chloride, esterification of L-tyrosine in MeOH in the presence of thionylchloride, and synthesis of the methyl ester of N-caproyl-Z,-prolyl-L-tyrosine by the mixed anhydride method using isobutylchloroformate in DMF. The active metabolite of dilept (N-caproyl-L-prolyl-Z,-tyrosine) was synthesized and characterized by physicochemical methods.