engleski

Use of Enantioselective Liquid Chromatography for Preparation of Pure Atenolol Enantiomers

The study reported here shows the practicable preparation of pure atenolol (1) enantiomers using the enantioselective liquid chromatography. For enantiomers of the final atenolol and intermediate ester 5 the successful separation and peaks shapes could not been obtained without diethylamine as the component in the mobile phase. That makes difficult the recycling of the three-component mobile phase, unavoidable step in simulated moving bed chromatography separation technology. The only suitable methodology for preparation of atenolol enantiomers was proved the synthesis from its N-benzyl-N-isopropyl precursor 6 and the chiral stationary phase Chiralpak AD was found as very convenient for preparative separation of these enantiomers. The enantiomeric purities and recovery of separated enantiomers of 6 were very high, allowed the high enantiomeric purities of the final products, ee's 99.3% for S- and 99.0% for R-atenolol. The chromatographic separation parameters, as well as solubility of racemate in the mobile phase, are the good bases for the further examination of possible scale-up resolution of compound 6.

atenolol; enantiomer; chiral separation; chromatography

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