Chiral Separation of $\beta$-Blockers after Derivatization with (-)-$\alpa$- Methoxy-$\alpa$-(trifuoromethyl)phenylacetyl Chloride by Gas Chromatography

  • Published : 2001.10.01

Abstract

Gas chromatographic method was investigated for the chiral separation of several $\beta$-blockeros(atenolol, betaxolol, bisoprolol, metoprolol and pindolol) using (-)-$\alpa$-methoxy-$\alpa$-(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 (-)-$\alpa$-methoxy-$\alpa$-(trifluoromethyl)phenylacetyl chloride was used as the chiral derivatizing agent. But in the opposite sequence when (+)-$\alpa$-methoxy-$\alpa$-(trifluoromethyl)phenylacetyl chloride was used. No racemization was found during the reaction.

Keywords

References

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