37787-63-6

Upstream product

• 195712-42-6 methyl 1,1-dioxo-2α-bromo-3-methyl-7-phenoxyacetamido-cephem-4-carboxylate 
• 10209-06-0 (6R,7R)-methyl 3-methyl-8-oxo-7-(2-phenoxyacetamido)-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate 
• 22252-43-3 3-deacetyloxy-7-aminocephalosporanic acid 
• 10209-11-7 (6R,7R)-3-Methyl-8-oxo-7-(2-phenoxy-acetylamino)-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid 
• 701-99-5 Phenoxyacetyl chloride 
• 37787-59-0 (6R)-3-methylene-5ξ,8-dioxo-7t-(2-phenoxy-acetylamino)-(6rH)-5λ⁴-thia-1-aza-bicyclo[4.2.0]octane-2c-carboxylic acid methyl ester 

Downstream Products

• 195712-42-6 methyl 1,1-dioxo-2α-bromo-3-methyl-7-phenoxyacetamido-cephem-4-carboxylate 
• 211613-14-8 methyl 4-bromo-5-[carboxy-(2-phenoxyacetamido)-methyl]-3-methyl-1H-pyrrole-2-carboxylate 
• 40849-62-5 (6R)-3t-methyl-5,5,8-trioxo-7t-(2-phenoxy-acetylamino)-(6rH)-5λ⁶-thia-1-aza-bicyclo[4.2.0]octane-2c-carboxylic acid methyl ester 

Relevant academic research and scientific papers

Reactions of cephalosporin sulfones 3. Synthesis of 2- phenylhydrazonocephem-sulfones. A new potential entry to 2-aminocephems [1]

Reaction of cephem sulfones 1a-e with aryldiazonium salts gives the 2-azo compounds which immediately rearrange into the corresponding 2-hydrazono derivatives 2a-e.

Reactions of cephalosporin sulphones 2. Rearrangement of 2α- bromocephem sulphones to pyrroles

2α-Bromocephem sulphones exhibit two different rearrangements in acetonitrile solution: first, the tendency for elimination of the bromine as a bromonium ion leads to its formal movement to the para position of the 7β- aromatic ring. Secondly, a bromopyrrole derivative may also form, which can possibly be attributed to an unusual Ramberg-Backlund-like rearrangement followed by bromination.