A practical synthesis of the RARγ agonist, BMS-270394

被引：13

作者：

Chidambaram, R ^{[1
]}

Kant, J

Zhu, J

Lajeunesse, J

Sirard, P

Ermann, P

Schierling, P

Lee, P

Kronenthal, D

机构：

[1] Bristol Myers Squibb Co, Dept Proc Res & Dev, New Brunswick, NJ 08903 USA

[2] Bristol Myers Squibb Co, Dept Proc Res & Dev, Candiac, PQ J5R 1J1, Canada

[3] DSM Fine Chem, Proc Res, D-93055 Regensburg, Germany

来源：

ORGANIC PROCESS RESEARCH & DEVELOPMENT | 2002年 / 6卷 / 05期

关键词：

D O I：

10.1021/op0202134

中图分类号：

O69 [应用化学];

学科分类号：

081704 ;

摘要：

A novel synthesis of 1 (BMS-270394), a nuclear retinoic acid receptor (RARgamma) agonist, is reported. The synthesis includes an enantioselective reduction of alpha-ketoacid 4 to the corresponding chiral a.-hydroxy acid 7 using a NaBH4/L-tartaric acid mixture and a novel coupling between 7 and an electron-deficient aniline 11 which was activated via N-sulfinyl derivative 15 to form chiral alpha-hydroxy amide 16. The synthesis was completed by a racemization-free hydrolysis of 16 to the corresponding alpha-hydroxy amidoacid 1 using KOPSiMe3 in acetonitrile.

引用

页码：632 / 636

页数：5

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