Development of a Scalable Synthetic Route to BMS-986251. Part 1: Synthesis of the Cyclohexane Dicarboxylate Fragment
Organic Process Research & Development(2021)
Abstract
The cyclohexane dicarboxylate unit of BMS-986251 (1), a potent and efficacious ROR gamma t inverse agonist, was synthesized starting from Hagemann's ester in seven chemical transformations with five isolated intermediates. The synthesis involved an enzymatic kinetic resolution, a two-step telescoped enol tosylation followed by carboxylation using a benign CO surrogate for the installation of the second carboxylate functionality, and a Crabtree catalyst-mediated diastereoselective olefin hydrogenation. This process was successfully demonstrated to produce 3.6 kg of compound 3.
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Key words
enzymatic ester hydrolysis,carboxylation using a CO surrogate,Crabtree hydrogenation,nuclear hormone receptors,ROR gamma t
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