A novel method for the preparation of a chiral stationary phase containing an enantiopure acridino-18-crown-6 ether selector

Tamás Németh; Sándor Lévai; Tamás Fődi; József Kupai; György Túrós; Tünde Tóth; Péter Huszthy; György Tibor Balogh

doi:10.1093/chromsci/bmu157

A novel method for the preparation of a chiral stationary phase containing an enantiopure acridino-18-crown-6 ether selector

J Chromatogr Sci. 2015 Mar;53(3):431-5. doi: 10.1093/chromsci/bmu157. Epub 2014 Dec 4.

Authors

Tamás Németh¹, Sándor Lévai², Tamás Fődi³, József Kupai¹, György Túrós⁴, Tünde Tóth¹, Péter Huszthy¹, György Tibor Balogh⁵

Affiliations

¹ Department of Organic Chemistry and Technology, Budapest University of Technology and Economics, PO Box 91, Budapest H-1521, Hungary.
² Compound Profiling Laboratory, Chemical Works of Gedeon Richter Plc., PO Box 27, Budapest H-1475, Hungary.
³ Department of Organic Chemistry and Technology, Budapest University of Technology and Economics, PO Box 91, Budapest H-1521, Hungary Compound Profiling Laboratory, Chemical Works of Gedeon Richter Plc., PO Box 27, Budapest H-1475, Hungary.
⁴ Medicinal Chemistry Laboratory II, Chemical Works of Gedeon Richter Plc., PO Box 27, Budapest H-1475, Hungary.
⁵ Compound Profiling Laboratory, Chemical Works of Gedeon Richter Plc., PO Box 27, Budapest H-1475, Hungary gy.balogh@richter.hu.

PMID: 25477392
DOI: 10.1093/chromsci/bmu157

Abstract

This paper reports a novel method for the preparation of chiral stationary phases (CSPs) using an acridino-18-crown-6 ether selector as a model compound. Chiral stationary phase (R,R)-CSP- 2A: was obtained by in situ continuously recirculating the solution of carboxyl-substituted acridino-18-crown-6 ether (R,R)- 4: , dicyclohexylcarbodiimide and 3-(triethoxysilyl)propylamine through a high-performance liquid chromatography (HPLC) column containing blank silica gel in elevated pressure and temperature. The enantiomer separating ability of chiral stationary phase (R,R)-CSP- 2A: was investigated by HPLC using mixtures of enantiomers of 1-(1-naphthyl)ethylamine hydrogen perchlorate, 1-(2-naphthyl)ethylamine, 1-(4-bromophenyl)ethylamine and 1-(4-nitrophenyl)ethylamine hydrogen chloride. The best results were found for the separation of the mixtures of enantiomers of Br-PEA.

Publication types

Evaluation Study
Research Support, Non-U.S. Gov't

MeSH terms

Amino Acids / chemistry*
Chromatography, High Pressure Liquid / instrumentation
Chromatography, High Pressure Liquid / methods*
Crown Ethers / chemistry*
Ether / chemistry*
Silica Gel / chemistry
Stereoisomerism

Substances

Amino Acids
Crown Ethers
Ether
Silica Gel
18-crown-6