ISSN:
0899-0042
Keywords:
oxazepam
;
3-O-acyloxazepam
;
racemization
;
kinetics
;
Chemistry
;
Organic Chemistry
Source:
Wiley InterScience Backfile Collection 1832-2000
Topics:
Chemistry and Pharmacology
Notes:
Enantiomers of 3-O-acyloxazepam (oxazepam 3-acetate; OXA) underwent base-catalyzed hydrolysis and racemization. Kinetics of reaction products formed from an OXA enantiomer in buffered and unbuffered alkaline solutions were analyzed by chiral stationary phase high-performance liquid chromatography. Racemization occurred with varying rates in aqueous solutions with pH ranging from 7.5 to 14. Racemization mechanism was studied by the dependence of rates of hydrolysis and racemization on temperature and pH. Mass spectral analysis of racemization products derived from an OXA enantiomer in a deuterated solvent indicated that racemization was accompanied by a proton exchange with the solvent. The results indicated that a base-catalyzed keto-enol tautomerism between the C2-carbonyl group and the C3 carbon was responsible for the observed racemization. © 1994 Wiley-Liss, Inc.This article is a US Goverment work and, as such, is in the public domain in the United States of America.
Additional Material:
11 Ill.
Type of Medium:
Electronic Resource
URL:
http://dx.doi.org/10.1002/chir.530060416
