Mild and Efficient DBU-Catalyzed Amidation of Cyanoacetates

Price, Kristin E.; Larrivée-Aboussafy, Claude; Lillie, Brett M.; McLaughlin, Robert W.; Mustakis, Jason; Hettenbach, Kevin W.; Hawkins, Joel M.; Vaidyanathan, Rajappa

doi:10.1021/ol900435t.s001

ol900435t_si_001.pdf (742.6 kB)

Mild and Efficient DBU-Catalyzed Amidation of Cyanoacetates

journal contribution

posted on 2009-05-07, 00:00 authored by Kristin E. Price, Claude Larrivée-Aboussafy, Brett M. Lillie, Robert W. McLaughlin, Jason Mustakis, Kevin W. Hettenbach, Joel M. Hawkins, Rajappa Vaidyanathan

A mild, high-yielding, and practical protocol for the direct amidation of alkyl cyanoacetates using DBU is presented. This method eliminates the need for activation of cyanoacetic acid and/or high temperatures. It has been applied to the large-scale synthesis of CP-690,550-10 (1), a compound under development for the treatment of autoimmune diseases.