1185886-67-2Relevant academic research and scientific papers
Remote electronic control in the regioselective reduction of succinimides: A practical, scalable synthesis of EP4 antagonist MF-310
Molinaro, Carmela,Gauvreau, Danny,Hughes, Gregory,Lau, Stephen,Lauzon, Sophie,Angelaud, Remy,O'Shea, Paul D.,Janey, Jacob,Palucki, Michael,Hoerrner, Scott R.,Raab, Conrad E.,Sidler, Rick R.,Belley, Michel,Han, Yongxin
supporting information; experimental part, p. 6863 - 6866 (2009/12/30)
(Chemical Equation Presented) A practical large-scale chromatography-free synthesis of EP4 antagonist MF-310, a potential new treatment for chronic inflammation, is presented. The synthetic route provided MF-310 as its sodium salt in 10 steps and 17% overall yield from commercially available pyridine dicarboxylate 7. The key features of this sequence include a unique regioselective reduction of succinimide 2 controlled by the electronic properties of a remote pyridine ring, preparation of cyclopropane carboxylic acid 3 via a Corey - Chaykovsky cyclopropanation, and a short synthesis of sulfonamide 5. 2009 American Chemical Society.
