Self-disproportionation of enantiomers of prazoles via achiral, gravity-driven silica gel column chromatography

(R)-Lansoprazole, (S)-pantoprazole, and (R)-rabeprazole are commonly used drugs for peptic ulcers. The self-disproportionation of the enantiomers of these prazoles in regular column chromatography is described herein. When non-racemic mixtures of the prazoles were eluted under achiral, gravity-drive...

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Bibliographic Details
Published in:Tetrahedron: asymmetry 2013-08, Vol.24 (15-16), p.909-912
Main Authors: Song, Weiguo, Zhou, Yuhan, Fu, Yongqiang, Xu, Wenfang
Format: Article
Language:English
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Summary:(R)-Lansoprazole, (S)-pantoprazole, and (R)-rabeprazole are commonly used drugs for peptic ulcers. The self-disproportionation of the enantiomers of these prazoles in regular column chromatography is described herein. When non-racemic mixtures of the prazoles were eluted under achiral, gravity-driven silica gel column chromatography conditions, enantiomeric enrichment occurred in the first fractions, while enantiomeric depletion occurred in the last fractions. The pure enantiomers of all prazoles can be prepared from non-racemic starting materials using a simple procedure (achiral chromatography). Thus, a new method for obtaining a sample with very high enantiomeric purity was established. These results suggested that caution is required to avoid enantiomer fractionation during the purification of the asymmetric synthesis products by chromatography.
ISSN:0957-4166
1362-511X
DOI:10.1016/j.tetasy.2013.06.008