title: Stereoselective Synthesis of HIV-1 Protease Inhibitor, DMP 323.
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.
authors.affiliation: Chemical Proces R&D Department, Process Research Facility, The DuPont Merck Pharmaceutical Company, Deepwater, New Jersey 08023-0999, and Chemical & Physical Sciences Department, The DuPont Merck Pharmaceutical Company, Experimental Station, Wilmington, Delaware 19880-0500.
authors.forename: Michael E.
authors.initials: ME
authors.lastname: Pierce
authors.forename: Gregory D.
authors.initials: GD
authors.lastname: Harris
authors.forename: Qamrul
authors.initials: Q
authors.lastname: Islam
authors.forename: Lilian A.
authors.initials: LA
authors.lastname: Radesca
authors.forename: Louis
authors.initials: L
authors.lastname: Storace
authors.forename: Robert E.
authors.initials: RE
authors.lastname: Waltermire
authors.forename: Ed
authors.initials: E
authors.lastname: Wat
authors.forename: Prabhakar K.
authors.initials: PK
authors.lastname: Jadhav
authors.forename: George C.
authors.initials: GC
authors.lastname: Emmett