Abstract
A new potential neuroleptic drug dilept (N-caproyl-L-prolyl-L-tyrosine methyl ester) has been created. This paper describes a 4-step scalable method of dilept synthesis, which provides a nonracemized product with 52% yield. The process includes caproic acid synthesis using thionyl chloride, acylation of proline by the obtained chloroanhydride under Schotten – Baumann reaction conditions, etherification of L-tyrosine in methyl alcohol in the presence of thionyl chloride, and synthesis of N-caproyl-L-prolyl-L-tyrosine methyl ester by the method of mixed anhydrides using isobutyl chloroformate in DMF. The active metabolite of dilept (N-caproyl-L-prolyl-L-tyrosine) has been also synthesized and characterized by physicochemical methods.
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