Organic Process Research and Development p. 66 - 81 (2014)
Update date:2022-07-31
Topics:
Bowles, Paul
Brenek, Steven J.
Caron, Stephane
Do, Nga M.
Drexler, Michele T.
Duan, Shengquan
Dube, Pascal
Hansen, Eric C.
Jones, Brian P.
Jones, Kris N.
Ljubicic, Tomislav A.
Makowski, Teresa W.
Mustakis, Jason
Nelson, Jade D.
Olivier, Mark
Peng, Zhihui
Perfect, Hahdi H.
Place, David W.
Ragan, John A.
Salisbury, John J.
Stanchina, Corey L.
Vanderplas, Brian C.
Webster, Mark E.
Weekly, R. Matt
A practical synthesis of SGLT2 inhibitor candidate ertugliflozin (1) has been developed for potential commercial application. The highly telescoped process involves only three intermediate isolations over a 12-step sequence. The dioxabicyclo[ 3.2.1]octane motif is prepared from commercially available 2,3,4,6-tetra-O-benzyl-D-glucose, with nucleophilic hydroxymethylation of a 5-ketogluconamide intermediate as a key step. The aglycone moiety is introduced via aryl anion addition to a methylpiperazine amide. High chemical purity of the API is assured through isolation of the crystalline penultimate intermediate, tetraacetate 39. A cocrystalline complex of the amorphous solid 1 with L-pyroglutamic acid has been prepared in order to improve the physical properties for manufacture and to ensure robust API quality.
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