39656-32-1

Upstream product

• 28180-82-7 2,2,2-trichloroethyl ester of 7-aminodeacetoxycephalosporanic acid 
• 555-16-8 4-nitrobenzaldehdye 

Downstream Products

• 40288-89-9 (6R)-3-methyl-7c-methylsulfanyl-7t-(4-nitro-benzylideneamino)-8-oxo-(6rH)-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid 2,2,2-trichloro-ethyl ester 
• 40288-92-4 (6R)-7c-methoxy-3-methyl-8-oxo-7t-(2-phenoxy-acetylamino)-(6rH)-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid 2,2,2-trichloro-ethyl ester 
• 64551-17-3 (6R)-7c-methoxy-3-methyl-8-oxo-7t-(2-phenoxy-acetylamino)-(6rH)-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid 
• 39741-93-0 (6R)-3-methyl-7-(4-nitro-benzylideneamino)-8-oxo-(6rH)-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2,7c-dicarboxylic acid bis-(2,2,2-trichloro-ethyl) ester 

Relevant academic research and scientific papers

7-Carboxy or 2,2,2-trichloroethoxy carbonyl- cephalosporins

6-APA, 7-ACA and 7-ADCA esters are reacted with benzaldehyde, acetophenone or substituted derivatives thereof providing imines which react in the presence of a strong base such as sodium hydride or lithium diisopropyl amide with a C2 -C5 alkanoyl halide, 2,2,2-trichloroethoxycarbonyl chloride, a benzoyl halide, a C1 -C4 alkoxycarbonyl chloride or a methoxymethyl halide to afford C6 and C7 substituted β-lactam imines via acylation or methoxymethylation. The β-lactam substituted imines are reacted with a carbonyl reagent, e.g. Girard's reagent T to provide a C6 substituted 6-APA ester or a C7 substituted 7-ACA or 7-ADCA ester which is acylated to provide a 6-acylamido-6-substituted penicillin or a 7-acyl-amide-7-substituted cephalosporin.