Journal
TETRAHEDRON
Volume 75, Issue 32, Pages 4351-4357Publisher
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tet.2019.04.057
Keywords
C-N coupling; N-arylation; Amino acids; Amidation; Stereocontrolled
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An efficient synthesis of PI3K inhibitor GDC-0077, featuring two consecutive Cu-catalyzed C-N coupling reactions, is reported. The described synthetic route involves a chemoselective Ullmann-type coupling of a chiral difluoromethyl-substituted oxazolidinone, a Cu-catalyzed N-arylation of L-alanine with high stereochemical integrity, and a high-yielding final amide bond formation step to produce GDC-0077 in >99.5 area % HPLC purity. (C) 2019 Elsevier Ltd. All rights reserved.
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