Development of a Scaleable Process for the Synthesis of the A2a Agonist, UK-371,104

…, LC Hesmondhalgh, P Pascal, AJ Pettman…

Index: Challenger, Stephen; Dessi, Yann; Fox, Darrell E.; Hesmondhalgh, Lynsey C.; Pascal, Pierre; Pettman, Alan J.; Smith, Julian D. Organic Process Research and Development, 2008 , vol. 12, # 4 p. 575 - 583

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Citation Number: 20

Abstract

The development and utilization of a scaleable process for the manufacture of the A2a agonist UK-371,104 (1) is described. Key steps in the synthesis include (i) a palladium- catalyzed cyanation reaction to prepare the nitrile 10,(ii) a telescoped conversion of the acid 11 to the glycosidation substrate 9, and (iii) the stereoselective coupling of 8 with 9 in a glycosidation reaction mediated by TMS triflate in 1, 2-dimethoxyethane followed by ...