Chiral Separation of β-Blockers after Derivatization with (-)-αMethoxy-α-(trifluoromethyl)phenylacetyl Chloride by Gas Chromatography

초록

Gas Chromatographic method was investigated for the chiral separation of several β-blockers(atenolol, betaxolol, bisoprolol, metoprolol and pindolol) using (-)-α-methoxy-α-(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-N-(trimethylsilyl)trifluoroacetamide. The reaction was selective and rapid and the diastereomeric derivatives were well separated by capillary gas chromatography. (R)-isomers were eluted faster than (S)-isomers when (-)-α-methoxy-α-(trifluoromethyl)phenylacetyl chloride was used as the chiral derivatizing agent. But in the opposite sequence when (+)-α-methoxy-α-(trifluoromethyl)phenylacetyl chloride was used. No racemization was found during the reaction.

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