PRODUCTION OF HALOGENATED BETA-LACTAM COMPOUND

PURPOSE: To obtain the subject compound in high yield and purity in a simple operation by halogenating the allenyl group of an allenyl β-lactam compound using a new halogenating reagent having high site selectivity. CONSTITUTION: A copper(II) halide or metal halide is made to act on the allenyl grou...

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Bibliographic Details
Main Authors TORII SHIGERU, TANAKA HIDEO, KAMEYAMA YUTAKA, SASAOKA MICHIO, SUZUKI DAISUKE
Format Patent
LanguageEnglish
Published 24.09.1996
Edition6
Subjects
CHEMISTRY
HETEROCYCLIC COMPOUNDS
METALLURGY
ORGANIC CHEMISTRY
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Summary:PURPOSE: To obtain the subject compound in high yield and purity in a simple operation by halogenating the allenyl group of an allenyl β-lactam compound using a new halogenating reagent having high site selectivity. CONSTITUTION: A copper(II) halide or metal halide is made to act on the allenyl group of a compound of formula I (R is H or amino; R is H, a halogen, etc.; R is H or a carboxyl group-protecting group; is a hydrocarbon or S-S(O)n -Ar; (n) is 0-2; Ar is an aryl) to obtain the objective halogenated β-lactam compound of formula II (X and Y are each a halogen). The amounts of the copper(II) halide (e.g. cupric chloride) and metal halide (e.g. calcium chloride) to be used are l-10 equivalents based on the compound of formula I, respectively, and the reaction is conducted in a solvent such as N,N-dimethylformamide at -78 to 60 deg.C. The compound of formula II is an important intermediate easily convertible into 3-norcephem, isocephem, etc.
Bibliography:Application Number: JP19950079489