Use of (S)-BINOL as NMR chiral solvating agent for the enantiodiscrimination of omeprazole and its analogs.
Chirality
; 22(5): 472-8, 2010 May 15.
Article
in En
| MEDLINE
| ID: mdl-19750547
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.
Full text:
1
Collection:
01-internacional
Database:
MEDLINE
Main subject:
Solvents
/
Omeprazole
/
Magnetic Resonance Spectroscopy
/
Naphthols
Language:
En
Journal:
Chirality
Journal subject:
BIOLOGIA MOLECULAR
/
QUIMICA
Year:
2010
Document type:
Article
Affiliation country:
Spain