Development of an Early-Phase Bulk Enabling Route to Sodium-Dependent Glucose Cotransporter 2 Inhibitor Ertugliflozin
Organic Process Research & Development2014Vol. 18(1), pp. 57–65
Citations Over TimeTop 10% of 2014 papers
David J. Bernhardson, Thomas A. Brandt, Catherine A. Hulford, Richard Lehner, Brian R. Preston, Kristin E. Price, John Sagal, Michael J. St. Pierre, Peter H. Thompson, Benjamin A. Thuma
Abstract
The development and optimization of a scalable synthesis of sodium-dependent glucose cotransporter 2 inhibitor, ertugliflozin, for the treatment of type-2 diabetes is described. Highlights of the chemistry are a concise, four-step synthesis of a structurally complex API from known intermediate 4 via persilylation–selective monodesilylation, primary alcohol oxidation, aldol-crossed-Cannizzaro reaction, and solid-phase acid-catalyzed bicyclic ketal formation. The final API was isolated as the l-pyroglutamic acid cocrystal.
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