Organic Chemistry

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

Authors

Abstract

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.

Content

Thumbnail image of 2020_03-31 Sulfenyl Chloride_Final.pdf

Supplementary material

Thumbnail image of 2020_03_31 Sulfenyl chloride SI FINAL.pdf
2020 03 31 Sulfenyl chloride SI FINAL