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Isolation and purification of (2R,3S)-3-phenylisoserine hydrochloride

Barbara Kąkol 1Magdalena Jezierska-Zięba 1Michał Fedoryński 2Jacek Cybulski 1

1. Industrial Chemistry Research Institute (ICRI), Rydygiera 8, Warszawa 01-793, Poland
2. Warsaw University of Technology, Faculty of Chemistry, Koszykowa 75, Warszawa 00-662, Poland

Abstract

The aim of this work was to develop a method of separation and purification of (2R,3S)-3-phenylisoserine hydrochloride (FIS), obtained from methyl N-acetyl-(2R,3S)-3-amino-2-hydroxy-3-phenyl propionate by acidic hydrolysis.

We found that isolation and purification of FIS can be effectively realised by extraction of impurities, present in the aqueous phase after acidic hydrolysis, by organic solvents. The best results were achieved using diethyl ether or t-butyl methyl ether as solvents. The aqueous phase after extraction was then evaporated to dryness. The crude solid FIS thus obtained crystallizes with difficulty from aqueous or alcoholic solutions. Good results of purification were obtained using n-propanol as a solvent, however the yield of crystallization was only 54%.

Removal of the impurities present in the solid FIS can be achieved much more efficiently by simple stirring of the solid with ethyl acetate or methylene chloride at 50 ºC for 2 hours. Using this procedure we obtained FIS with 90% purity and 95% purification yield.

 

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Submitted: 2008-03-14 08:38
Revised:   2009-06-07 00:48