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Use of (S)-BINOL as NMR chiral solvating agent for the enantiodiscrimination of omeprazole and its analogs

✍ Scribed by Jordi Redondo; Anna Capdevila; Isabel Latorre

Publisher
John Wiley and Sons
Year
2009
Tongue
English
Weight
330 KB
Volume
22
Category
Article
ISSN
0899-0042

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✦ Synopsis

Abstract

The application of (S)‐1,1′‐binaphthyl‐2,2′‐diol as NMR chiral solvating agent (CSA) for omeprazole, and three of its analogs (lanso‐, panto‐, and rabe‐prazole) was investigated. The formation of diastereomeric host–guest complexes in solution between the CSA and the racemic substrates produced sufficient NMR signal splitting for the determination of enantiomeric excesses by ^1^H‐ or ^19^F‐NMR spectroscopy. Using of hydrophobic deuterated solvents was mandatory for obtaining good enantiodiscrimination, thus suggesting the importance of intermolecular hydrogen bonds in the stabilization of the complexes. The method was applied to the fast quantification of the enantiomeric purity of in‐process samples of S‐omeprazole. Chirality, 2010. © 2009 Wiley‐Liss, Inc.

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The use of organometallic CDAs based on ethene-platinum(II) complexes, covalent cis- and trans-dichloro(Am)(ethylene)platinum(II), and ionic [PtCl(3)(C(2)H(4))](-)[AmH](+), containing primary and secondary amines, for the (195)Pt NMR enantiodiscrimination of chiral unsaturated compounds is reviewed.