Synthesis of Filibuvir. Part III. Development of a Process for the Reductive Coupling of an Aldehyde and a β-Keto-lactone
Organic Process Research & Development2013Vol. 18(1), pp. 45–56
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Nathan D. Ide, John A. Ragan, Gabriel Bellavance, Steve J. Brenek, Eric M. Cordi, Grace O. Jensen, Kris Jones, Danny Lafrance, Kyle R. Leeman, Leo J. Letendre, D.W. Place, Corey L. Stanchina, Gregory W. Sluggett, Holly Strohmeyer, Jon Blunt, Kevin Meldrum, Stuart A. Taylor, Ciaran Byrne, Denis Lynch, Sandra Mullane, Maria M. O’Sullivan, Marcella Whelan
Abstract
Development of a reductive coupling of a β-keto-lactone and an aldehyde is described, in which the Hantzsch ester serves as an inexpensive and convenient reducing agent. Structural features in the β-keto-lactone rendered standard reductive coupling conditions ineffective, requiring development of a specific addition and temperature protocol. Identification of one of the reactants as Ames positive required a single-digit parts per million control strategy for this impurity in the final active pharmaceutical ingredient (API).
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