Application of the Schopf method to optimization of the synthesis of 3-[2-(p-N-acetylaminophenyl)ethyl]-3-hydroxy-4-methylpentanoic acid: Simultaneous reduction of three functional groups to maximize yield and throughput

Authors
Deering, CF Huckabee, BK Lin, SC Porter, KT Rossman, CA Wemple, J
Citation
Cf. Deering et al., Application of the Schopf method to optimization of the synthesis of 3-[2-(p-N-acetylaminophenyl)ethyl]-3-hydroxy-4-methylpentanoic acid: Simultaneous reduction of three functional groups to maximize yield and throughput, ORG PROC R, 4(6), 2000, pp. 596-600
Citations number
12
Categorie Soggetti
Organic Chemistry/Polymer Science
Journal title
ORGANIC PROCESS RESEARCH & DEVELOPMENT
ISSN journal
10836160 → ACNP
Volume
4
Issue
6
Year of publication
2000
Pages
596 - 600
Database
ISI
SICI code
1083-6160(200011/12)4:6<596:AOTSMT>2.0.ZU;2-K
Abstract
Application of the Schopf method to development of a high yield condensatio n process to prepare a labile beta-(p-nitrophenyl)-alpha,beta -unsaturated ketone system, along with development of a procedure for simultaneous hydro genation/hydrogenolysis of olefin, benzyl ester, and nitro groups, allows t he construction of an inexpensive route to 3-[2-(p-N-acetylaminophenyl)ethy l]-3-hydroxy-4-methylpentanoic acid, a key intermediate in the preparation of CI-1029 and related HIV protease inhibitors.