Abstract
Chloroquine (CQ) was found to exhibit antiviral activity against novel coronaviruses, which makes the preparation of CQ enantiomers particularly important. In this work, we developed an efficient method for the preparation of CQ enantiomers by crystallization resolution and palladium-catalyzed coupling. The obtained chiral CQ had been fully assigned by 1H-1H COSY, 1H-13C HSQC, and 1H-13C HMBC spectra. Moreover, the enantiomeric excess value of CQ was rapidly detected by binaphthol phosphate as a chiral NMR shift reagent.
Keywords: Chloroquine, Crystallization resolution, Palladium-catalyzed coupling, Single enantiomer, NMR determination, Chiral shift reagent.
Letters in Organic Chemistry
Title:Efficient Preparation of Chloroquine Enantiomers via Crystallization Resolution and Palladium-Catalysed Coupling
Volume: 20
Author(s): Shanshan Sun, Xuming Sha, Bowen Han, Dandan Guo and Shaohua Huang*
Affiliation:
- Institute of Drug Discovery Technology, Ningbo University, Ningbo 315211, PR China
- Qian Xuesen Collaborative Research Center of Astrochemistry and Space Life Sciences, Ningbo University, Ningbo, Zhejiang, PR China
Keywords: Chloroquine, Crystallization resolution, Palladium-catalyzed coupling, Single enantiomer, NMR determination, Chiral shift reagent.
Abstract: Chloroquine (CQ) was found to exhibit antiviral activity against novel coronaviruses, which makes the preparation of CQ enantiomers particularly important. In this work, we developed an efficient method for the preparation of CQ enantiomers by crystallization resolution and palladium-catalyzed coupling. The obtained chiral CQ had been fully assigned by 1H-1H COSY, 1H-13C HSQC, and 1H-13C HMBC spectra. Moreover, the enantiomeric excess value of CQ was rapidly detected by binaphthol phosphate as a chiral NMR shift reagent.
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Cite this article as:
Sun Shanshan, Sha Xuming, Han Bowen, Guo Dandan and Huang Shaohua*, Efficient Preparation of Chloroquine Enantiomers via Crystallization Resolution and Palladium-Catalysed Coupling, Letters in Organic Chemistry 2023; 20 () . https://dx.doi.org/10.2174/1570178620666230125140838
DOI https://dx.doi.org/10.2174/1570178620666230125140838 |
Print ISSN 1570-1786 |
Publisher Name Bentham Science Publisher |
Online ISSN 1875-6255 |
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