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KMID : 0043320010240050402
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Archives of Pharmacal Research
2001 Volume.24 No. 5 p.402 ~ p.406
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Chiral Separation of β-Blockers after Derivatization with (-)-- Methoxy--(trifuoromethyl)phenylacetyl Chloride by Gas Chromatography
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Kim Kyeong-Ho
Lee Joo-Hyun
Ko Mi-Young
Hong Seon-Pyo
Youm Jeong-Rok
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Abstract
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Gas chromatographic method was investigated for the chiral separation of several -blockeros(atenolol, betaxolol, bisoprolol, metoprolol and pindolol) using (-)--methoxy--(trifluoromethyl)phenylacetyl chloride as a chiral derivatizing agent for amino group. Prior to N-acylation, hydroxyl group was converted into O-silyl ethers by react with N-methyl-H-(taimethylsilyl)trifluoroacetamide. The reaction was selective and rapid and the diasteromeric derivatives were well separated by capillary gas chromatography. (R)-isomers were eluted faster than (S)-isomers when (-)--methoxy--(trifluoromethyl)phenylacetyl chloride was used as the chiral derivatizing agent. But in the opposite sequence when (+)--methoxy--(trifluoromethyl)phenylacetyl chloride was used. No racemization was found during the reaction.
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KEYWORD
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Chiral derivatization, β-Blockers, Gas chromatography, Resolution, (-)--methoxy--(trifluoromethyl) phenylacetyl ch loride
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