Epimerization of Benzylpenicilloic Acid in Alkaline Media

□ 5R,6R -Benzylpenicilloic acid was found to epimerize slowly in alkaline media to 5S,6R-benzylpenicilloic acid until equilibrium was established. Epimerization proceeded via the imine tautomer of penamaldic acid rather than the enamine form and was found to favor the 5S,6R-epimer at equilibrium. Th...

Full description

Saved in:
Bibliographic Details
Published in:Journal of pharmaceutical sciences 1984-01, Vol.73 (1), p.125-128
Main Authors: Ghebre-Sellassie, Isaac, Hem, Stanley L., Knevel, Adelbert M.
Format: Article
Language:English
Subjects:
alkaline media
Benzylpenicilloic acid-epimerization
Benzylpenicilloic acid—epimerization, alkaline media, imine tautomer of penamaldic acid as intermediate
Chemical Phenomena
Chemistry
Chromatography, High Pressure Liquid
Epimerization-benzylpenicilloic acid in alkaline media
Epimerization—benzylpenicilloic acid in alkaline media, imine tautomer of penamaldic acid as intermediate
Exact sciences and technology
Heterocyclic compounds
Heterocyclic compounds with n hetero atom and also o and/or s, se, te hetero atoms
Hydrogen-Ion Concentration
imine tautomer of penamaldic acid as intermediate
intermediate in the epimerization of benzylpenicilloic acid
Magnetic Resonance Spectroscopy
Organic chemistry
Penamaldic acid-imine tautomer
Penamaldic acid—imine tautomer, intermediate in the epimerization of benzylpenicilloic acid
Penicillin G - analogs & derivatives
Penicillin G - analysis
Polarography
Preparations and properties
Spectrophotometry, Ultraviolet
Stereoisomerism
Citations: Items that this one cites
Items that cite this one
Online Access:Get full text
Tags: Add Tag
No Tags, Be the first to tag this record!
Description
Summary:□ 5R,6R -Benzylpenicilloic acid was found to epimerize slowly in alkaline media to 5S,6R-benzylpenicilloic acid until equilibrium was established. Epimerization proceeded via the imine tautomer of penamaldic acid rather than the enamine form and was found to favor the 5S,6R-epimer at equilibrium. The conversion process was monitored using both reverse-phase high-performance liquid chromatography and NMR spectroscopy.
ISSN:0022-3549
1520-6017
DOI:10.1002/jps.2600730135