A Practical Synthesis of the RARγ Agonist, BMS-270394
Organic Process Research & Development2002Vol. 6(5), pp. 632–636
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Ramakrishnan Chidambaram, Joydeep Kant, Jason Zhu, Jean Lajeunesse, Pierre Sirard, P. Ermann, Peter Schierling, Peter Lee, David R. Kronenthal
Abstract
A novel synthesis of 1 (BMS-270394), a nuclear retinoic acid receptor (RARγ) agonist, is reported. The synthesis includes an enantioselective reduction of α-ketoacid 4 to the corresponding chiral α-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 α-hydroxy amide 16. The synthesis was completed by a racemization-free hydrolysis of 16 to the corresponding α-hydroxy amidoacid 1 using KOSiMe3 in acetonitrile.
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