Literature DB >> 33664631

A High-Yielding Synthesis of EIDD-2801 from Uridine.

Alexander Steiner1,2, Desiree Znidar1,2, Sándor B Ötvös1,2, David R Snead3, Doris Dallinger1,2, C Oliver Kappe1,2.   

Abstract

A simple reordering of the reaction sequence allowed the improved synthesis of EIDD-2801, an antiviral drug with promising activity against the SARS-CoV-2 virus, starting from uridine. Compared to the original route, the yield was enhanced from 17 % to 61 %, and fewer isolation/purification steps were needed. In addition, a continuous flow procedure for the final acetonide deprotection was developed, which proved to be favorable toward selectivity and reproducibility.
© 2020 The Authors. European Journal of Organic Chemistry published by Wiley‐VCH GmbH.

Entities:  

Keywords:  Acetonide deprotection; COVID‐19; Continuous flow; EIDD‐2801; Triazolation

Year:  2020        PMID： 33664631      PMCID： PMC7894511          DOI： 10.1002/ejoc.202001340

Source DB:  PubMed          Journal:  European J Org Chem        ISSN： 1099-0690


  3 in total

Review 1.  Continuous-flow technology—a tool for the safe manufacturing of active pharmaceutical ingredients.

Authors:  Bernhard Gutmann; David Cantillo; C Oliver Kappe
Journal:  Angew Chem Int Ed Engl       Date:  2015-05-18       Impact factor: 15.336

2.  A concise route to MK-4482 (EIDD-2801) from cytidine.

Authors:  N Vasudevan; Grace P Ahlqvist; Catherine P McGeough; Dinesh J Paymode; Flavio S P Cardoso; Tobias Lucas; Jule-Phillip Dietz; Till Opatz; Timothy F Jamison; Frank B Gupton; David R Snead
Journal:  Chem Commun (Camb)       Date:  2020-10-08       Impact factor: 6.222

3.  The Hitchhiker's Guide to Flow Chemistry ∥.

Authors:  Matthew B Plutschack; Bartholomäus Pieber; Kerry Gilmore; Peter H Seeberger
Journal:  Chem Rev       Date:  2017-06-01       Impact factor: 60.622
  3 in total
  8 in total

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4.  An Engineered Cytidine Deaminase for Biocatalytic Production of a Key Intermediate of the Covid-19 Antiviral Molnupiravir.

Authors:  Ashleigh J Burke; William R Birmingham; Ying Zhuo; Thomas W Thorpe; Bruna Zucoloto da Costa; Rebecca Crawshaw; Ian Rowles; James D Finnigan; Carl Young; Gregory M Holgate; Mark P Muldowney; Simon J Charnock; Sarah L Lovelock; Nicholas J Turner; Anthony P Green
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5.  Cost of Goods Analysis Facilitates an Integrated Approach to Identifying Alternative Synthesis Methodologies for Lower Cost Manufacturing of the COVID-19 Antiviral Molnupiravir.

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Review 7.  Toward a Practical, Nonenzymatic Process for Investigational COVID-19 Antiviral Molnupiravir from Cytidine: Supply-Centered Synthesis.

Authors:  Vijayagopal Gopalsamuthiram; Appasaheb L Kadam; Jeffrey K Noble; David R Snead; Corshai Williams; Timothy F Jamison; Chris Senanayake; Ajay K Yadaw; Sarabindu Roy; Gopal Sirasani; B Frank Gupton; Justina Burns; Daniel W Cook; Rodger W Stringham; Saeed Ahmad; Rudy Krack
Journal:  Org Process Res Dev       Date:  2021-12-09       Impact factor: 3.317

Review 8.  A comprehensive update on the structure and synthesis of potential drug targets for combating the coronavirus pandemic caused by SARS-CoV-2.

Authors:  Prerna Malik; Sonika Jain; Pankaj Jain; Jyoti Kumawat; Jaya Dwivedi; Dharma Kishore
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  8 in total

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