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

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%.