Journal of Organic Chemistry 2001-01-01

Stereoselective Synthesis of HIV-1 Protease Inhibitor, DMP 323.

MichaelE. Pierce, GregoryD. Harris, Qamrul Islam, LilianA. Radesca, Louis Storace, RobertE. Waltermire, Ed Wat, PrabhakarK. Jadhav, GeorgeC. Emmett

Index: J. Org. Chem. 61 , 444, (1996)

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Abstract

DMP 323, a potent HIV-1 protease inhibitor, has been synthesized by an efficient stereoselective process, amenable to large scale preparations. The core C(2) symmetric diol was synthesized by a stereoselective pinacol coupling of CBZ protected D-phenylalanine. Judicious selection of protecting groups allowed cyclic urea formation under mild conditions, enhanced the ease of bis-alkylation, and led to intermediates which were easily purified without chromatography. Additionally, a one-pot, high yield process was developed to prepare the alkylating agent, 4-[(triphenylmethoxy)methyl]benzyl chloride from 1,4-benzenedimethanol.