Ontology highlight
ABSTRACT:
SUBMITTER: de Souza JM
PROVIDER: S-EPMC7574626 | biostudies-literature | 2020 Oct
REPOSITORIES: biostudies-literature
de Souza Juliana M JM Berton Mateo M Snead David R DR McQuade D Tyler DT
Organic process research & development 20200513 10
We demonstrate a continuous two-step sequence in which sulfenyl chloride is formed, trapped by vinyl acetate, and chlorinated further via a Pummerer rearrangement. These reactions produce a key intermediate in our new approach to the oxathiolane core used to prepare the antiretroviral medicines emtricitabine and lamivudine. During batch scale-up to tens of grams, we found that the sequence featured a strong exotherm and evolution of hydrogen chloride and sulfur dioxide. Keeping gaseous byproduct ...[more]