64276-70-6

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 
• 103-82-2 phenylacetic acid 
• 908093-98-1 diazodiphenylmethane 
• 103-80-0 phenylacetyl chloride 
• 15690-38-7 (6R,7R)-7-amino-3-hydroxymethyl-8-oxo-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid 
• 5350-57-2 benzophenone hydrazone 
• 28240-15-5 3-hydroxymethyl-8-oxo-7-phenylacetylamino-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid 

Downstream Products

• 129849-19-0 (6R,7R)-3-Allyl-8-oxo-7-phenylacetylamino-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid benzhydryl ester 
• 123201-39-8 diphenylmethyl 7β-[2-(2-tritylaminothiazol-4-yl)-(Z)-2-tritylhydroxyimino]-3-vinyl-3-cephem-4-carboxylate 
• 128454-32-0 7β-[(Z)-2-(2-amino-4-thiazolyl)-2-(trityloxyamino)acetamido]-3-vinylcephem-4-carboxylic acid 
• 91832-40-5 cefdinir 
• 94796-13-1 diphenylmethyl 7β-phenylacetamido-3-vinyl-3-cephem-4-carboxylate 

Relevant academic research and scientific papers

An alternative procedure for preparation of cefdinir

Cefdinir, a broad spectrum third-generation cephalosporin for oral administration, was prepared by the following synthetic pathway: synthesis of diphenylmethyl 7β-amino-3-vinyl-3-cephem-4-carboxylate hydrochloride from 7-aminocephalosporanic acid (7-ACA), preparation of sodium 2-(2-tritylaminothiazol-4-yl)-(Z)-2-(tritylhydroxyimino) acetate from ethyl acetoacetate, coupling of both intermediaries to obtain diphenylmethyl 7β-[2-(2-tritylaminothiazol-4-yl)-(Z)-2-tritylhydroxyimino-3- vinyl-3-cephem-4-carboxylate and final cleavage of trityl and diphenylmethyl protective groups. This procedure allows to obtain better yields of cefdinir and to avoid the use of diketene during the synthesis of this antibiotic by the previously reported method.