Toward a Practical, Nonenzymatic Process for Investigational COVID-19 Antiviral Molnupiravir from Cytidine: Supply-Centered Synthesis
Name
acs.oprd.1c00219.pdf
Description
Published version
Size
1.02 MB
Format
Adobe PDF
Checksum (MD5)
1398aec0c417d24cf6a8e125aa1b7f18
Author(s)
Gopalsamuthiram, Vijayagopal
Kadam, Appasaheb L
Noble, Jeffrey K
Snead, David R
Williams, Corshai
Jamison, Timothy F
Senanayake, Chris
Yadaw, Ajay K
Roy, Sarabindu
Sirasani, Gopal
Date Issued
December 17, 2021
Journal
Organic Process Research & Development
Publisher
American Chemical Society (ACS)
Citation
Gopalsamuthiram, Vijayagopal, Kadam, Appasaheb L, Noble, Jeffrey K, Snead, David R, Williams, Corshai et al. 2021. "Toward a Practical, Nonenzymatic Process for Investigational COVID-19 Antiviral Molnupiravir from Cytidine: Supply-Centered Synthesis." Organic Process Research & Development, 25 (12).
Version
Final published version
Abstract
A scalable four-step synthesis of molnupiravir from cytidine is described herein. The attractiveness of this approach is its fully chemical nature involving inexpensive reagents and more environmentally friendly solvents such as water, isopropanol, acetonitrile, and acetone. Isolation and purification procedures are improved in comparison to our earlier study as all intermediates can be isolated via recrystallization. The key steps in the synthesis, namely, ester formation, hydroxyamination, and deprotection were carried out on a multigram scale to afford molnupiravir in 36-41% yield with an average purity of 98 wt % by qNMR and 99 area% by HPLC.
MIT Department
Massachusetts Institute of Technology. Department of Chemistry
Terms of Use
Creative Commons Attribution-NonCommercial-NoDerivs License
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DOI of Published Version
https://doi.org/10.1021/acs.oprd.1c00219
