406-11-1Relevant academic research and scientific papers
Development of a Scalable Enantioselective Synthesis of JAK Inhibitor Upadacitinib
Bhagavatula, Lakshmi,Christesen, Alan,Dunn, Travis B.,Ickes, Andrew,Kotecki, Brian J.,Marek, James C.,Morrill, Westin H.,Moschetta, Eric,Mulhern, Mathew,Rasmussen, Michael,Reynolds, Troy,Rozema, Michael J.,Yu, Su
, (2021/10/21)
Process development of a six-stage synthesis of upadacitinib, a JAK1 inhibitor, is described. It is highlighted by an enantioselective and diastereoselective hydrogenation of a tetrasubstituted olefin to set the two pyrrolidine stereocenters. Preparation of the main fragments and strategies to link them together, optimization of the imidazole cyclization, and in-depth understanding of the formation of the urea moiety at the final stage are discussed.
Scavenging of fluorinated N,N′-dialkylureas by hydrogen binding: A novel separation method for fluorous synthesis
Palomo, Claudio,Aizpurua, Jesus M.,Loinaz, Iraida,Fernandez-Berridi, Maria Jose,Irusta, Lourdes
, p. 2361 - 2364 (2007/10/03)
(matrix presented) A dramatic solubility increase in fluorous solvents is observed for N,N′-di(polyfluoroalkyl)ureas when hydrogen binding complexes are formed with commercially available perfluoroalkanoic acid scavengers. As a case example, analytically pure peptides and esters are obtained using this novel separation method.
Nona and decapeptide analogs of LHRH useful as LHRH antagonists
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, (2008/06/13)
Synthetic nonapeptide and decapeptide LHRH antagonist analogues having a halo lower alkyl guanadino-substituted amino acyl residue at position six are disclosed herein.
