Oxidative removal of p-methoxybenzyl-amino protecting group in the presence of a proximal hydroxy function: A solution to a process problem in SUSTIVA (R) (efavirenz) synthesis

Authors
Choudhury, A Pierce, ME Confalone, PN
Citation
A. Choudhury et al., Oxidative removal of p-methoxybenzyl-amino protecting group in the presence of a proximal hydroxy function: A solution to a process problem in SUSTIVA (R) (efavirenz) synthesis, SYN COMMUN, 31(23), 2001, pp. 3707-3714
Citations number
14
Categorie Soggetti
Organic Chemistry/Polymer Science
Journal title
SYNTHETIC COMMUNICATIONS
ISSN journal
00397911 → ACNP
Volume
31
Issue
23
Year of publication
2001
Pages
3707 - 3714
Database
ISI
SICI code
0039-7911(2001)31:23<3707:OROPPG>2.0.ZU;2-6
Abstract
A practical and scaleable synthetic procedure for the deprotection of a p-m ethoxy benzyl group from the tertiary carbinol 2 in the commercial synthesi s of SUSTIVA (R) (efavirenz) I is described. The methodology involves a two step, one pot operation with an isolated yield of 82.5% with a product pur ity of > 99.5%.