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Synthesis of an Oxathiolane Drug Substance Intermediate Guided by Constraint Driven Innovation

preprint
submitted on 01.04.2020 and posted on 02.04.2020 by Komirishetty Kashinath, David Snead, Justina Burns, Rodger W. Stringham, B. Frank Gupton, D. Tyler McQuade
A new route was developed for construction of the oxathiolane intermediate used in the synthesis of lamivudine (3TC) and emtricitabine (FTC). We developed the presented route by constraining ourselves to low cost, widely available starting materials – we refer to this as supply centered synthesis. Sulfenyl chloride chemistry was used to construct the framework for the oxathiolane from acyclic precurors. This bond construction choice enabled the use of chloroacetic acid, vinyl acetate, sodium thiosulfate and water to produce the oxathiolane.

Funding

Bill and Melinda Gates Foundation

History

Email Address of Submitting Author

drsnead@vcu.edu

Institution

Virginia Commonwealth University

Country

USA

ORCID For Submitting Author

0000-0003-1239-533X

Declaration of Conflict of Interest

No conflict of interest

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