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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
Analytical Science and Technology / Analytical Science and Technology, (P)1225-0163; (E)2288-8985
2021, v.34 no.1, pp.9-16
https://doi.org/10.5806/AST.2021.34.1.9
(College of Pharmacy, Kangwon National University)
(Faculty of Pharmacy, Ho Chi Minh City University of Technology)
(College of Pharmacy, Kangwon National University)
(College of Pharmacy, Kangwon National University)
(Faculty of Pharmacy, Ho Chi Minh City University of Technology)
(College of Pharmacy, Kangwon National University)
(College of Pharmacy, Kangwon National University)
Sang,
H.
S.
, Xuan-Lan,
M.
, Thi-Anh-Tuyet,
L.
, &
Kyeong,
H.
K.
(2021). 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. Analytical Science and Technology, 34(1), 9-16, https://doi.org/10.5806/AST.2021.34.1.9
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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
- <TEX>${\beta}$</TEX>-blockers, Chiral derivatizing agent, <TEX>$^1H$</TEX>-NMR, HPLC
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