High-Yielding Synthesis of Antiviral Drug Candidate

  • Author: European Journal of Organic Chemistry
  • Published Date: 19 November 2020
  • Copyright: Wiley-VCH GmbH
thumbnail image: High-Yielding Synthesis of Antiviral Drug Candidate

Related Societies

The COVID-19 pandemic is caused by the coronavirus SARS-CoV-2. Drugs for the treatment of this disease are urgently needed. The antiviral compound EIDD-2801 (molnupiravir, pictured above) has been identified as a potential drug candidate against COVID-19 and is currently in phase II clinical trials. The existing route for its synthesis, however, gives EIDD-2801 from uridine in a rather low yield of 17 %.


C. Oliver Kappe, Doris Dallinger, University of Graz, Austria, and colleagues have developed an improved synthesis of EIDD-2801 from uridine (pictured below) by strategically reordering the synthetic steps. The reaction sequence starts with the activation of uridine with 1,2,4-triazole and continues with a telescoped acetonide protection/esterification and a telescoped hydroxyamination/acetonide deprotection. Telescoped reaction sequences consist of two or more than one one-pot procedures that are performed back-to-back without a work-up step in-between. A continuous flow process was used for the final acetonide deprotection, which improved selectivity and reproducibility.

 


Compared to the original route, the yield of EIDD-2801 was improved to 61 %. This strategy also requires fewer isolation steps because of the two telescoped procedures (acetonide protection/esterification and hydroxyamination/acetonide deprotection) included within the five‐step route.


 

 

Article Views: 882

Sign in Area

Please sign in below

Additional Sign In options

Please note that to comment on an article you must be registered and logged in.
Registration is for free, you may already be registered to receive, e.g., the newsletter. When you register on this website, please ensure you view our terms and conditions. All comments are subject to moderation.

Article Comments - To add a comment please sign in

If you would like to reuse any content, in print or online, from ChemistryViews.org, please contact us first for permission. more

Follow on Facebook Follow on Twitter Follow on YouTube Follow on LinkedIn Follow on Instagram RSS Sign up for newsletters

Magazine of Chemistry Europe (16 European Chemical Societies) published by Wiley-VCH