PRACTICAL SYNTHESIS, SEPARATION, AND STEREOCHEMICAL ASSIGNMENT OF THE PMPA PRO-DRUG GS-7340

H. Chapman Gilead Sciences, 333 Lakeside Drive, Foster City, California, 94404, U.S.A.

M. Kernan Gilead Sciences, 333 Lakeside Drive, Foster City, California, 94404, U.S.A.

E. Prisbe Gilead Sciences, 333 Lakeside Drive, Foster City, California, 94404, U.S.A.

J. Rohloff Gilead Sciences, 333 Lakeside Drive, Foster City, California, 94404, U.S.A.

M. Sparacino Gilead Sciences, 333 Lakeside Drive, Foster City, California, 94404, U.S.A.

T. Terhorst Gilead Sciences, 333 Lakeside Drive, Foster City, California, 94404, U.S.A.

R. Yu Gilead Sciences, 333 Lakeside Drive, Foster City, California, 94404, U.S.A.

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Abstract

The practical synthesis of a mixed phenoxy-amidate derivative of PMPA with high oral bioavailability and favorable pharmacokinetics is described. The non-stereoselective synthetic route produces a 1:1 mixture of two diastereomers at phosphorous. Simulated moving bed chromatography using Chiralpak AS enabled kilo-scale isolation of the more potent diastereomer (GS-7340). The GS-7340 phosphorous chiral center was found to be (S) by X-ray crystallography.

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PRACTICAL SYNTHESIS, SEPARATION, AND STEREOCHEMICAL ASSIGNMENT OF THE PMPA PRO-DRUG GS-7340

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PRACTICAL SYNTHESIS, SEPARATION, AND STEREOCHEMICAL ASSIGNMENT OF THE PMPA PRO-DRUG GS-7340

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