Stereoselective synthesis of renin inhibitor BILA 2157 BS

Authors
Simoneau, B Lavallee, P Bailey, M Duceppe, JS Grand-Maetre, C Grenier, L Ogilvie, WW Poupart, MA Thavonekham, B
Citation
B. Simoneau et al., Stereoselective synthesis of renin inhibitor BILA 2157 BS, CAN J CHEM, 78(6), 2000, pp. 739-748
Citations number
10
Categorie Soggetti
Chemistry
Journal title
CANADIAN JOURNAL OF CHEMISTRY-REVUE CANADIENNE DE CHIMIE
ISSN journal
00084042 → ACNP
Volume
78
Issue
6
Year of publication
2000
Pages
739 - 748
Database
ISI
SICI code
0008-4042(200006)78:6<739:SSORIB>2.0.ZU;2-0
Abstract
We have developed a convergent and stereoselective synthesis of orally acti ve renin inhibitor BILA 2157 BS. Three building blocks were used to generat e the basic skeleton of the inhibitor. The key feature consisted of the lat e elaboration of the 2-amino-4-thiazolyl heterocycle from a vinylbromide pr ecursor. The synthetic sequence, which required a total of 22 chemical step s, provided 0.6 kg of BILA 2157 BS in 7.3% overall yield.