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Spectroscopic identification of intermediates and final products of the chiral pool synthesis of sutezolid

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cris.lastimport.scopus2024-02-12T20:52:31Z
dc.abstract.enSutezolid is a new oxazolidinone derivative currently in clinical trials to determine its safety and efficacy towards highly drug-resistant tuberculosis. The aim of the study was the spectroscopic identification of selected key intermediate products of the chiral pool synthesis of sutezolid: (S1) (4-(2-fluoro-4-nitrophenyl)thiomorpholine), (S2) 4-[2-fluoro-4-(benzyloxycarbonyl)aminophenyl] thiomorpholine, (S4) (R)-[[3-[3-fluoro-4-(4-thiomorpholinyl)phenyl]-2-oxo-5-oxazolidinyl]methyl]-p-toluenesulfonate, (S5) (R)-[[3-(3-fluoro-4-(4-thiomorpholinyl)phenyl]-2-oxo-5-oxazolidinyl]methyl]azide, as well as (S6) sutezolid, the final synthesis product. Spectroscopic identification was carried out based on infrared spectra analysis (FT-IR) and Raman scattering. This part of the analysis was supported by quantum chemical calculations based on the density functional theory (DFT) utilizing the B3LYP hybrid functional and the 6-31G(d,p) basis set to obtain reference standards for intermediates and sutezolid. Additionally, the sutezolid configuration was confirmed by analysing the electronic circular dichroism (ECD) spectra of (S)- and (R)- isomers, combined with the time-dependent DFT calculations to simulate ECD spectra depending on the solvent and type of conformers.
dc.affiliationUniwersytet Warszawski
dc.contributor.authorMizera, Mikołaj
dc.contributor.authorPałys, Barbara
dc.contributor.authorCielecka-Piontek, Judyta
dc.contributor.authorBocian, Wojciech
dc.contributor.authorMichalska, Katarzyna
dc.contributor.authorLewandowska, Kornelia
dc.date.accessioned2024-01-26T07:55:26Z
dc.date.available2024-01-26T07:55:26Z
dc.date.issued2020
dc.description.financePublikacja bezkosztowa
dc.description.volume1217
dc.identifier.doi10.1016/J.MOLSTRUC.2020.128396
dc.identifier.issn0022-2860
dc.identifier.urihttps://repozytorium.uw.edu.pl//handle/item/120340
dc.identifier.weblinkhttps://api.elsevier.com/content/article/PII:S0022286020307213?httpAccept=text/xml
dc.languageeng
dc.pbn.affiliationchemical sciences
dc.relation.ispartofJournal of Molecular Structure
dc.relation.pages128396
dc.rightsClosedAccess
dc.sciencecloudnosend
dc.subject.enECD
dc.subject.enFT-IR
dc.subject.enRaman scattering
dc.subject.enSutezolid
dc.titleSpectroscopic identification of intermediates and final products of the chiral pool synthesis of sutezolid
dc.typeJournalArticle
dspace.entity.typePublication