Cyrene as a bio-based solvent for HATU mediated amide coupling

Wilson, Kirsty L. and Murray, Jane and Jamieson, Craig and Watson, Allan J. B. (2018) Cyrene as a bio-based solvent for HATU mediated amide coupling. Organic and Biomolecular Chemistry (16). pp. 2851-2854. ISSN 1477-0520

[img]
Preview
 Text (Wilson-etal-OBC2018-Cyrene-as-a-bio-based-solvent-for-HATU-mediated-amide-coupling)
Wilson_etal_OBC2018_Cyrene_as_a_bio_based_solvent_for_HATU_mediated_amide_coupling.pdf
Accepted Author Manuscript
Download (848kB)| Preview

    Abstract

    Amide bonds are one of the underpinning linkages in all living systems and are fundamental within drug discovery. Current methods towards their synthesis frequently rely on the use of dipolar aprotic solvents; however, due to increasingly stringent regulations and growing societal pressures, safe and more sustainable alternatives are highly sought after. Herein, we evaluate the application of the bio-based solvent Cyrene™ in the HATU mediated synthesis of amides and peptides. We found that Cyrene functioned as a competent replacement for DMF in the synthesis of a series of lead-like compounds and dipeptides (25 examples, 63–100%).

    Creators(s): Wilson, Kirsty L. ORCID logoORCID: https://orcid.org/0000-0002-4382-6246, Murray, Jane, Jamieson, Craig ORCID logoORCID: https://orcid.org/0000-0002-6567-8272 and Watson, Allan J. B.;
    Item type:Article
    ID code:65939
    Keywords:amide bonds, drug discovery, cyrene, biomolecular chemistry, Chemistry, Biochemistry, Organic Chemistry, Physical and Theoretical Chemistry
    Subjects:Science > Chemistry
    Department:Faculty of Science > Pure and Applied Chemistry
    Depositing user: Pure Administrator
    Date deposited:01 Nov 2018 10:18
    Last modified:25 Sep 2020 03:08
    Related URLs:
    URI:https://strathprints.strath.ac.uk/id/eprint/65939
    Export data:
    CORE (COnnecting REpositories)