Scale-up and optimization of a continuous flow synthesis of an α-thio-βchloroacrylamide

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dc.contributor.authorDennehy, Olga C.
dc.contributor.authorLynch, Denis
dc.contributor.authorCollins, Stuart G.
dc.contributor.authorMaguire, Anita R.
dc.contributor.authorMoynihan, Humphrey A.
dc.contributor.funderScience Foundation Irelanden
dc.contributor.funderEuropean Regional Development Funden
dc.date.accessioned2020-05-25T09:38:28Z
dc.date.available2020-05-25T09:38:28Z
dc.date.issued2020-05-19
dc.description.abstractUse of continuous flow processing to undertake a multistep chlorination cascade has been achieved with effective inline work-up and end-of-line crystallization in batch leading to isolation of α-thio-β-chloroacrylamide Z-3 in pure form from a complex reaction mixture, exploiting the advantage of efficient heat transfer in flow. During the development of a continuous flow strategy for the production of appreciable quantities of the α-thio-β-chloroacrylamides, difficulties surrounding a labour and resource intensive work-up followed by final product isolation were addressed. A greener solvent choice was applied to the chemical synthesis which enabled inline purification and separation, resulting in the crystallization of pure product directly from the reaction mixture. This process was readily scalable and demonstrated control over impurity formation and removal, which is key in an industrial setting.en
dc.description.sponsorshipScience Foundation Ireland and the European Regional Development Fund (Synthesis and Solid State Pharmaceutical Centre: SFI SSPC3 Pharm5 12/RC/2275_2)en
dc.description.statusPeer revieweden
dc.description.versionAccepted Versionen
dc.format.mimetypeapplication/pdfen
dc.identifier.citationDennehy, O. C., Lynch, D., Collins, S. G., Maguire, A. R. and Moynihan, H. A. (2020) ‘Scale-up and optimization of a continuous flow synthesis of an α-thio-β-chloroacrylamide’, Organic Process Research and Development. doi: 10.1021/acs.oprd.0c00079en
dc.identifier.doi10.1021/acs.oprd.0c00079en
dc.identifier.eissn1520-586X
dc.identifier.issn1083-6160
dc.identifier.journaltitleOrganic Process Research and Developmenten
dc.identifier.urihttps://hdl.handle.net/10468/10023
dc.language.isoenen
dc.publisherAmerican Chemical Societyen
dc.relation.projectinfo:eu-repo/grantAgreement/SFI/SFI Research Centres/12/RC/2275/IE/Synthesis and Solid State Pharmaceutical Centre (SSPC)/en
dc.relation.projectinfo:eu-repo/grantAgreement/SFI/SFI Research Infrastructure Programme/15/RI/3221/IE/Process Flow Spectroscopy (ProSpect); Advanced Reaction Understanding using Flow Nuclear Magnetic Resonance (NMR) and Infrared (IR) Spectroscopies, with On-Line Ultra-Performance Liquid Chromatography (UPLC) and Mass Spectrometry (MS)/en
dc.rights© 2020, American Chemical Society. This document is the Accepted Manuscript version of a Published Work that appeared in final form in Organic Process Research and Development after technical editing by the publisher. To access the final edited and published work see https://pubs.acs.org/doi/abs/10.1021/acs.oprd.0c00079en
dc.subjectContinuous processingen
dc.subjectFlow chemistryen
dc.subjectProcess impuritiesen
dc.subjectα-thio-βchloroacrylamidesen
dc.titleScale-up and optimization of a continuous flow synthesis of an α-thio-βchloroacrylamideen
dc.typeArticle (peer-reviewed)en
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