128454-32-0

Basic information

• Product Name: 7β-[(Z)-2-(2-amino-4-thiazolyl)-2-(trityloxyamino)acetamido]-3-vinylcephem-4-carboxylic acid
• Synonyms: 7β-[(Z)-2-(2-amino-4-thiazolyl)-2-(trityloxyamino)acetamido]-3-vinylcephem-4-carboxylic acid
• CAS NO: 128454-32-0
• Molecular Weight: 637.74
• Mol File: 128454-32-0.mol

Chemical Properties

• CAS DataBase Reference: 7β-[(Z)-2-(2-amino-4-thiazolyl)-2-(trityloxyamino)acetamido]-3-vinylcephem-4-carboxylic acid(CAS DataBase Reference)
• NIST Chemistry Reference: 7β-[(Z)-2-(2-amino-4-thiazolyl)-2-(trityloxyamino)acetamido]-3-vinylcephem-4-carboxylic acid(128454-32-0)
• EPA Substance Registry System: 7β-[(Z)-2-(2-amino-4-thiazolyl)-2-(trityloxyamino)acetamido]-3-vinylcephem-4-carboxylic acid(128454-32-0)

Safety Data

• Hazardous Substances Data: 128454-32-0(Hazardous Substances Data)

Upstream product

• 123201-39-8 diphenylmethyl 7β-[2-(2-tritylaminothiazol-4-yl)-(Z)-2-tritylhydroxyimino]-3-vinyl-3-cephem-4-carboxylate 
• 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 
• 94796-13-1 diphenylmethyl 7β-phenylacetamido-3-vinyl-3-cephem-4-carboxylate 
• 69689-86-7 ethyl 2-(2-tritylaminothiazol-4-yl)-(Z)-2-(tritylhydroxyimino)acetate 
• 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 
• 28240-15-5 3-hydroxymethyl-8-oxo-7-phenylacetylamino-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid 
• 64485-82-1 (Z)-ethyl 2-(2-aminothiazol-4-yl)-2-hydroxyiminoacetate 
• 64276-70-6 (6R,7R)-3-Bromomethyl-8-oxo-7-phenylacetylamino-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid benzhydryl ester 

Downstream Products

• 91832-40-5 cefdinir 
• 71091-93-5 3-methyl cefdinir 
• 934986-48-8 Cefdinir sulfoxide 

Relevant articles and documents

Novel compounds for the synthesis of Cefdinir

(Chemical Equation Presented) Preparation of two new compounds 2-mercapto-5-methyl-1,3,4-thiadiazolyl-(Z)-2-(2-amino-4-thiazolyl) -2-trityloxyiminoacetate (14) and 2-mercapto-5-methyl-1, 3,4-thiadiazolyl- (Z)-2-(2-amino-4-thiazolyl)-2-acetyloxyiminoacetate (12) and their use in the preparation of 7β-[(Z)-2-(2-amino-4-thiazolyl)-2-hydroxyiminoacetamido]-3- vinylcephem-4-carboxylic acid, also known by the generic name Cefdinir (1) has been accomplished in a single step by coupling with 7-amino-3-vinylcephem-4- carboxylic acid (7) with purity of greater than 99% by HPLC.

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.