27266-51-9

Basic information

• Product Name: (6R)-3-acetoxymethyl-7t-amino-8-oxo-(6rH)-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid benzyl ester
• CAS NO: 27266-51-9
• Molecular Weight: 362.406
• Mol File: 27266-51-9.mol
• Article Data: 2

Chemical Properties

• CAS DataBase Reference: (6R)-3-acetoxymethyl-7t-amino-8-oxo-(6rH)-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid benzyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: (6R)-3-acetoxymethyl-7t-amino-8-oxo-(6rH)-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid benzyl ester(27266-51-9)
• EPA Substance Registry System: (6R)-3-acetoxymethyl-7t-amino-8-oxo-(6rH)-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid benzyl ester(27266-51-9)

Safety Data

• Hazardous Substances Data: 27266-51-9(Hazardous Substances Data)

Upstream product

• 27285-69-4 (6R)-3-acetoxymethyl-7t-((R)-5-benzyloxycarbonyl-5-tert-butoxycarbonylamino-pentanoylamino)-8-oxo-(6rH)-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid benzyl ester 
• 27266-52-0 N-(tert-butoxycarbonyl)cephalosporin C 
• 51762-04-0 (6R)-3-acetoxymethyl-7t-((R)-5-amino-5-carboxy-pentanoylamino)-8-oxo-(6rH)-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid; monosodium salt 
• 27266-53-1 (6R)-3-acetoxymethyl-7t-((R)-5-amino-5-benzyloxycarbonyl-pentanoylamino)-8-oxo-(6rH)-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid benzyl ester 

Downstream Products

• 18884-61-2 (6R)-3-acetoxymethyl-7t-amino-8-oxo-(6rH)-5-thia-1-aza-bicyclo[4.2.0]oct-3-ene-2ξ-carboxylic acid benzyl ester 
• 16361-70-9 (6R)-3-acetoxymethyl-7t-[3-(2-chloro-ethyl)-ureido]-8-oxo-(6rH)-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid benzyl ester 

Relevant articles and documents

Process for the preparation of 7-aminocephalosporanic acids

7-Aminocephalosporanic acid (7-ACA) and 7-amino-3-methyl-3-cephem-4-carboxylic acid (7-ADCA) are valuable intermediates in the preparation of semi-synthetic cephalosporins. These compounds are commonly prepared by cleaving the amide bond of compounds having the formula SPC1 In which R6 is H or EQU1 R is the side chain of a known penicillin, especially phenoxymethyl or benzyl, and the amino and carboxyl functions are blocked; by A. halogenating the blocked compounds Ia or IIa to produce an imino-halide; B. forming an imino-ether from the imino-halide by treatment with an alcohol; and C. mixing said imino-ether with water or an alcohol to produce 7-aminocephalosporanic acid or 7-amino-3-methyl-3-cephem-4-carboxylic acid. The invention claimed is the use of dicyclohexylamine or diisopropylamine instead of a tertiary amine acid scavenger in step A.