Evidence map›Paper›PMID 34955627›Full record

ReviewOrganic process research & development2021

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

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 and 6 more

Abstract readReview
In one paragraph

Review in Organic process research & development, 2021. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 3 papers.

0numbers the graph read from it
0cells of the map it votes in
3citing papers in PubMed
–field-weighted citation impact
1 · What the graph read from it

What it found

Each row is one number read from the abstract, on the scale the paper reported it, with its interval. Left of the dashed line favours the treatment, right favours the comparator. Under each row is the sentence it came from. New to these charts? A ten-minute tutorial.

The abstract states no effect estimate the extractor could read, or names no intervention and outcome on the map, so this paper lights no cell and moves no belief. It is still indexed, cited and linked below.

2 · The registry

The trial behind it

Trials whose registry record cites this paper, or whose number appears in the abstract. A trial that started after this paper was published is citing it as background, not reporting it.

Neither the registry nor the abstract names a trial number. If this is a trial report, that itself is worth knowing.

3 · Its place in the literature

Who cites it

3 citing papers in PubMed.

  1. Article
  2. Article
  3. Review on molnupiravir as a promising oral drug for the treatment of COVID-19.Medicinal chemistry research : an international journal for rapid communications on design and mechanisms of action of biologically active agents · 2022
    Review
4 · The record

Corrections and comments

PubMed lists nothing against this paper. Absence here is not a guarantee, only a check that was made.

5 · Who and what money

Authors and funding

16 authors.

Vijayagopal GopalsamuthiramMedicines for All Institute, 737 N 5th Street, Box 980100, Richmond, Virginia 23298, United States.ORCID https://orcid.org/0000-0003-1483-6178
Appasaheb L KadamMedicines for All Institute, 737 N 5th Street, Box 980100, Richmond, Virginia 23298, United States.ORCID https://orcid.org/0000-0002-0452-2901
Jeffrey K NobleMedicines for All Institute, 737 N 5th Street, Box 980100, Richmond, Virginia 23298, United States.
David R SneadMedicines for All Institute, 737 N 5th Street, Box 980100, Richmond, Virginia 23298, United States.ORCID https://orcid.org/0000-0003-1239-533X
Corshai WilliamsDepartment of Chemistry, Massachusetts Institute of Technology, 77 Massachusetts Avenue, Cambridge, Massachusetts 02139, United States.
Timothy F JamisonDepartment of Chemistry, Massachusetts Institute of Technology, 77 Massachusetts Avenue, Cambridge, Massachusetts 02139, United States.
Chris SenanayakeTCG Green Chem, Inc, Process R & D Center, Princeton South, Ewing, New Jersey 08628, United States.
Ajay K YadawTCG Green Chem, Inc, Process R & D Center, Princeton South, Ewing, New Jersey 08628, United States.
Sarabindu RoyTCG Green Chem, Inc, Process R & D Center, Princeton South, Ewing, New Jersey 08628, United States.
Gopal SirasaniTCG Green Chem, Inc, Process R & D Center, Princeton South, Ewing, New Jersey 08628, United States.
B Frank GuptonMedicines for All Institute, 737 N 5th Street, Box 980100, Richmond, Virginia 23298, United States.ORCID https://orcid.org/0000-0002-8165-1088
Justina BurnsMedicines for All Institute, 737 N 5th Street, Box 980100, Richmond, Virginia 23298, United States.
Daniel W CookMedicines for All Institute, 737 N 5th Street, Box 980100, Richmond, Virginia 23298, United States.ORCID https://orcid.org/0000-0003-0621-3624
Rodger W StringhamMedicines for All Institute, 737 N 5th Street, Box 980100, Richmond, Virginia 23298, United States.
Saeed AhmadMedicines for All Institute, 737 N 5th Street, Box 980100, Richmond, Virginia 23298, United States.
Rudy KrackMedicines for All Institute, 737 N 5th Street, Box 980100, Richmond, Virginia 23298, United States.

Funding

No grant is acknowledged in the PubMed record.

6 · The paper itself

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.

Identifiers

PMID34955627
PMCPMC8689649

What OpenQuestion holds

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LicenceCC BY-NC-ND
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Registered trials

None linked

Read under generation 80e0d062 · epoch 390. Bibliography from PubMed, PubMed Central and OpenAlex; grants from NIH RePORTER; trial links from ClinicalTrials.gov; estimates, votes and beliefs from the OpenQuestion graph.