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Chiral Separation of Beta-Blockers After Derivatization With (-)-Alphamethoxy-Alpha-(Trifluoromethyl)phenylacetyl Chloride by Gas Chromatography

Chiral Separation of Beta-Blockers After Derivatization With (-)-Alphamethoxy-Alpha-(Trifluoromethyl)phenylacetyl Chloride by Gas Chromatography

K H Kim, J H Lee, M Y Ko, S P Hong, J R Youm

Arch Pharm Res. 2001 Oct;24(5):402-6.

PMID: 11693539

Abstract:

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

Chemicals Related in the Paper:

Catalog Number	Product Name	Structure	CAS Number	Price
AP20445334	(S)-(+)-α-Methoxy-α-(trifluoromethyl)phenylacetyl chloride		20445-33-4	Price

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