851-59-2

Upstream product

• 35246-64-1 (6R,7R)-benzhydryl 3-(hydroxymethyl)-8-oxo-7-(2-phenylacetamido)-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate 
• 859-07-4 cephaloram 
• 805-64-1 (6R)-3-acetoxymethyl-8-oxo-7t-(2-phenyl-acetylamino)-(6rH)-5-thia-1-aza-bicyclo[4.2.0]oct-3-ene-2ξ-carboxylic acid 
• 7629-50-7 (6R)-3-hydroxymethyl-8-oxo-7t-(2-phenyl-acetylamino)-(6rH)-5-thia-1-aza-bicyclo[4.2.0]oct-3-ene-2ξ-carboxylic acid 

Downstream Products

• 1214226-58-0 (6R,7R)-7-benzylcarbonylamino-3-formyl-8-oxo-5-thia-1-aza-bicyclo[4.2.0.]oct-2-ene-2-carboxylic acid benzhydryl ester 
• 71847-54-6 N-(5-Bromo-1,7-dioxo-2,2a,5,7-tetrahydro-1H,4H-6-oxa-3-thia-7b-aza-cyclobuta[e]inden-2-yl)-2-phenyl-acetamide 
• 56984-16-8 N-(5-Hydroxy-1,7-dioxo-2,2a,5,7-tetrahydro-1H,4H-6-oxa-3-thia-7b-aza-cyclobuta[e]inden-2-yl)-2-phenyl-acetamide 

Relevant academic research and scientific papers

An improved process for the preparation of diphenylmethyl7β- Phenylacetamido-3-hydroxymethyl-3-cephem-4-carboxylate

An efficient and improved process for the preparation of diphenylmethyl 7-phenylacetamido-3-hydroxymethyl-3-cephem-4-carboxylate was developed. With the commercially available 7-aminocephalosporanic acid (7-ACA) as starting material, up to 73.5% overall isolated yield of the titled compound was synthesized in two steps via direct phenylacetylation with phenylacetyl chloride, followed by basic hydrolysis and esterification with diphenyldiazomethane. The newly developed process obviated the use of protecting groups, reduced the environmental footprint, and could be easily controlled and conveniently scaled up for this pivotal intermediate in cephalosporin chemistry.

Process for preparing cephem lactones for cephalosporin-type antibiotics

Cephem lactones of formula (1) STR1 wherein R1 is hydrogen or an organic substituent of the type appearing as the 6-substituent of penicillins or as the 7-substituent of cephalosporins are produced from corresponding 4,5-halohydrin precursors thereof by dehalogenation. Novel stereoisomers of formula (1) compounds as well as novel intermediates for cephem lactone syntheses are disclosed. The cephem lactones produced according to the invention are of utility as intermediates for cephem-type antibiotics and have antibiotic properties of their own.