78183-91-2

Basic information

• Product Name: 4'-nitrobenzyl 3-methyl-2-(2-chlorosulfinyl-4-oxo-3-phenoxyacetamido-1-azetidinyl)-3-butenoate
• Synonyms: 4'-nitrobenzyl 3-methyl-2-(2-chlorosulfinyl-4-oxo-3-phenoxyacetamido-1-azetidinyl)-3-butenoate
• CAS NO: 78183-91-2
• Molecular Weight: 535.962
• Mol File: 78183-91-2.mol
• Article Data: 5

Chemical Properties

• CAS DataBase Reference: 4'-nitrobenzyl 3-methyl-2-(2-chlorosulfinyl-4-oxo-3-phenoxyacetamido-1-azetidinyl)-3-butenoate(CAS DataBase Reference)
• NIST Chemistry Reference: 4'-nitrobenzyl 3-methyl-2-(2-chlorosulfinyl-4-oxo-3-phenoxyacetamido-1-azetidinyl)-3-butenoate(78183-91-2)
• EPA Substance Registry System: 4'-nitrobenzyl 3-methyl-2-(2-chlorosulfinyl-4-oxo-3-phenoxyacetamido-1-azetidinyl)-3-butenoate(78183-91-2)

Safety Data

• Hazardous Substances Data: 78183-91-2(Hazardous Substances Data)

Upstream product

• 3481-09-2 N-chlorophthalimide 

Downstream Products

• 78109-48-5 p-nitrobenzyl 3-methyl-2-(2-oxo-4-sulfino-3-phenoxyacetamido-1-azetidinyl)-3-butenoate 
• 78183-93-4 3-Methyl-2-((1S,5R)-7-oxo-3-phenoxymethyl-4-oxa-2,6-diaza-bicyclo[3.2.0]hept-2-en-6-yl)-but-3-enoic acid 4-nitro-benzyl ester 
• 78109-50-9 p-Nitrobenzyl 3-methyl-2-(2-oxo-4-bromo-3-phenoxyacetamido-1-azetidinyl)-3-butenoate 
• 78109-51-0 p-Nitrobenzyl 3-methyl-2-(2-oxo-4-iodo-3-phenoxyacetamido-1-azetidinyl)-3-butenoate 
• 78109-49-6 2-[(2R,3R)-2-Fluoro-4-oxo-3-(2-phenoxy-acetylamino)-azetidin-1-yl]-3-methyl-but-3-enoic acid 4-nitro-benzyl ester 
• 78183-92-3 2-[(2R,3S)-2-Chloro-4-oxo-3-(2-phenoxy-acetylamino)-azetidin-1-yl]-3-methyl-but-3-enoic acid 4-nitro-benzyl ester 
• 78183-92-3 2-[(2R,3R)-2-Chloro-4-oxo-3-(2-phenoxy-acetylamino)-azetidin-1-yl]-3-methyl-but-3-enoic acid 4-nitro-benzyl ester 
• 61335-89-5 4'-Nitrobenzyl 3-methyl-2-(2-acetylhydrazosulfinyl-4-oxo-3-phenoxyacetamido-1-azetidinyl)-3-butenoate 
• 29707-62-8 6-(phenoxyacetamido)penicillanate sulfoxide p-nitrobenzyl ester 
• 61335-91-9 4'-Nitrobenzyl 3-methyl-2-(2-aminosulfinyl-4-oxo-3-phenoxyacetamido-1-azetidinyl)-3-butenoate 
• 61335-84-0 4'-Nitrobenzyl 3-methyl-2-(2-anilinosulfinyl-4-oxo-3-phenoxyacetamido-1-azetidinyl)-3-butenoate 

Relevant articles and documents

Method for the preparation of 2-chloro sulfinyl azetidinones

An improved method for the preparation of 2-chloro sulfinyl azetidin-4-one of the formula: STR1 wherein R is: hydrogen; C1 -C3 alkyl; halomethyl; cyanomethyl; phenyl; substituted phenyl; phenoxy, benzyloxy- or substituted benzyl; a group of the formula R2 --O--wherein R2 is t-butyl, 2,2,2-trichloroethyl, benzyl or substituted benzyl; a group of the formula R3 --(O)n --CH2 wherein R3 is phenyl or substituted phenyl. The 2-chlorosulfinylazetidin-4-one is prepared by reacting a penicillin sulfoxide ester of the general formula STR2 wherein R and R1 have the meanings defined above with an N-chloro halogenating agent in an inert organic solvent. The reaction is carried out in the presence of an acid scavenging amount of a phosphate or hydrogen phosphate of an alkali metal, alkaline earth metal, ammonium, quaternary ammonium or mixtures thereof. These compounds find application as intermediates in the production of cefaclor which are powerful anti-bacterial compounds.

Process for preparing 2-chlorosulfinylazetidinones

Improved process for converting a penicillin sulfoxide ester to a 2-chlorosulfinylazetidin-4-one intermediate which on cyclization affords a 3-exomethylenecepham sulfoxide, wherein the penicillin sulfoxide ester is reacted with an N-chloro halogenating agent in the presence of a cross-linked polyvinylpyridine polymer to provide the 2-chlorosulfinylazetidin-4-one.

Method of preparation of 3-methylenecephams

Penicillin sulfoxide derived azetidinone sulfinyl chlorides and related sulfinic acid derivatives are cyclized to 3-methylenecephams by reaction with Friedel-Crafts catalysts or metathetic cation forming agents.