NMR Studies of Drugs. Achiral and Chiral Lanthanide Shift Reagents with Mephenoxalone, a Substituted 2-Oxazolidinone

Autor:	Robert Rothchild, Stacey Traviglia, Kunisi S. Venkatasubban, Shari Braddock, Kerry Sanders
Rok vydání:	1993
Předmět:	Lanthanide Stereochemistry Aryl chemistry.chemical_element Medicinal chemistry Atomic and Molecular Physics and Optics Analytical Chemistry chemistry.chemical_compound chemistry Reagent Proton NMR medicine Mephenoxalone Enantiomer Europium Enantiomeric excess Spectroscopy medicine.drug
Zdroj:	Spectroscopy Letters. 26:271-291
ISSN:	1532-2289 0038-7010
DOI:	10.1080/00387019308011531
Popis:	The 1H NMR spectra of the skeletal muscle relaxant, mephenoxalone, 1, 5-[(2-methoxyphenoxy) - methyl]-2-oxazolidinone, have been studied at 200 MHz in CDCl3 solution at 20° in the presence of the achiral lanthanide shift reagent, tris(6,6,7,7,8,8,8-heptafluoro-2,2-dimethyl-3,5-octanedionato) europium (III), 2, and the chiral reagent, tris[3-(heptafluoropropylhydroxymethylene)-(+)-camphorato]europium(III), 3. Both reagents 2 or 3 produced significant lanthanide induced shifts for spectral simplification suggesting major lanthanide binding at the carbonyl. With 3, enantiomeric shift differences were observed for the signals of the NH, OCH3, methine CHO, both protons of the CH2O and one proton of the CH2N, and the aryl proton H-6. Direct determinations of enantiomeric excess of samples of 1 appear feasible by use of 3.
Databáze:	OpenAIRE
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