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http://dx.doi.org/10.5806/AST.2021.34.1.9

1H-NMR and HPLC analysis on the chiral discrimination of β-blockers using (S)-2-tert-butyl-2-methyl-1,3-benzodioxole-4-carboxylic acid  

Seo, Sang Hun (College of Pharmacy, Kangwon National University)
Mai, Xuan-Lan (Faculty of Pharmacy, Ho Chi Minh City University of Technology (HUTECH))
Le, Thi-Anh-Tuyet (College of Pharmacy, Kangwon National University)
Kim, Kyeong Ho (College of Pharmacy, Kangwon National University)
Publication Information
Analytical Science and Technology / v.34, no.1, 2021 , pp. 9-16 More about this Journal
Abstract
In the group of commonly prescribed β-blocker drugs, one of the enantiomers is generally relatively more active than the others. This study aims to develop a technique for the chiral analysis of select β-blockers based on proton nuclear magnetic resonance (1H-NMR) spectrometry. (S)-2-Tert-butyl-2-methyl-1,3-benzodioxole-4-carboxylic acid ((S)-TBMB) was synthesized and utilized as a chiral derivatizing agent. Pure β-blocker enantiomers were isolated from racemates by semi-preparative liquid chromatography prior to derivatization. The reaction time and concentration of (S)-TBMB were controlled to improve the derivatization procedure. No racemization was found during the analysis. High-performance liquid chromatography (HPLC) analysis was also performed for comparative purposes. High agreement between the NMR and HPLC methods was achieved in the determination of (R)-metoprolol in a standard solution of the (S) isomer.
Keywords
${\beta}$-blockers; Chiral derivatizing agent; $^1H$-NMR; HPLC;
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