1416247-69-2Relevant academic research and scientific papers
The large-scale synthesis of (S)-N-boc-bis(4-fluorophenyl)alanine
Appell, Robert B.,Boulton, Lee T.,Daugs, Edward D.,Hansen, Matt,Hanson, Christopher H.,Heinrich, Jerry,Kronig, Christel,Lloyd, Richard C.,Louks, David,Nitz, Mark,Praquin, Celine,Ramsden, James A.,Samuel, Helen,Smit, Mark,Willets, Matthew
, p. 69 - 76 (2013/03/13)
The synthesis of (S)-N-Boc-bis(4-fluorophenyl)alanine, an intermediate in the synthesis of denagliptin, is described from the synthesis of a 12 g proof of principle sample to a >900 kg cGMP manufacturing campaign. The chiral centre was established by the asymmetric hydrogenation of the sterically crowded precursor, ethyl 2-acetamido-3,3-bis(4-fluorophenyl)acrylate. The ability to isolate the various intermediates in a physical form that would readily allow filtration, washing, and ultimately purification underpinned the successful manufacturing campaign.
