Isolation and structure elucidation of a novel product of the acidic degradation of cefaclor.
The acidic aqueous degradation of cefaclor, an orally administered cephalosporin antibiotic, has been investigated. The most prominent peak in the high-performance liquid chromatography profile of a degraded solution of cefaclor was isolated by preparative high-performance liquid chromatography. Mechanistically, the formation of this degradent from cefaclor involves a condensation of two cefaclor degradation products in which both products have undergone contraction from a six-membered cephem ring to a five-membered thiazole ring, presumably via a common episulfonium ion intermediate.
Baertschi
S W
SW
Lilly Research Laboratories, Eli Lilly and Company, Lilly Corporate Center, Indianapolis, IN 46285-0724.
Dorman
D E
DE
Occolowitz
J L
JL
Spangle
L A
LA
Collins
M W
MW
Wildfeuer
M E
ME
Lorenz
L J
LJ
D002433:Cefaclor / Q000737:chemistry* / Q000302:isolation & purification; D002851:Chromatography, High Pressure Liquid; D006851:Hydrochloric Acid; D009682:Magnetic Resonance Spectroscopy; D016339:Spectrometry, Mass, Fast Atom Bombardment; D013055:Spectrophotometry, Infrared; D013056:Spectrophotometry, Ultraviolet
D002433:Cefaclor; D006851:Hydrochloric Acid