OXIDATIVE REMOVAL OF p-METH-OXYBENZYL-AMINO PROTECTING GROUP IN THE PRESENCE OF A PROXIMAL HYDROXY FUNCTION: A SOLUTION TO A PROCESS PROBLEM IN SUSTIVA® (EFAVIRENZ) SYNTHESIS

Anusuya Choudhury Chemical Process R&D Department, Process Research Facility, DuPont Pharmaceuticals Company, Deepwater, New Jersey, 08023-0999, U.S.A.

Michael E. Pierce Chemical Process R&D Department, Process Research Facility, DuPont Pharmaceuticals Company, Deepwater, New Jersey, 08023-0999, U.S.A.

Pat N. Confalone Chemical Process R&D Department, Process Research Facility, DuPont Pharmaceuticals Company, Deepwater, New Jersey, 08023-0999, U.S.A.

Abstract

A practical and scaleable synthetic procedure for the deprotection of a p-methoxy benzyl group from the tertiary carbinol 2 in the commercial synthesis of SUSTIVA® (efavirenz) 1 is described. The methodology involves a two step, one pot operation with an isolated yield of 82.5% with a product purity of > 99.5%.

ACKNOWLEDGMENT

We thank Dr. Rodger Stringham, Barbara Lord and Bill Cummings for their analytical support.

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OXIDATIVE REMOVAL OF p-METH-OXYBENZYL-AMINO PROTECTING GROUP IN THE PRESENCE OF A PROXIMAL HYDROXY FUNCTION: A SOLUTION TO A PROCESS PROBLEM IN SUSTIVA® (EFAVIRENZ) SYNTHESIS

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OXIDATIVE REMOVAL OF p-METH-OXYBENZYL-AMINO PROTECTING GROUP IN THE PRESENCE OF A PROXIMAL HYDROXY FUNCTION: A SOLUTION TO A PROCESS PROBLEM IN SUSTIVA® (EFAVIRENZ) SYNTHESIS

Abstract

ACKNOWLEDGMENT

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