67366-01-2

Upstream product

• 957-68-6 7-Aminocephalosporanic acid 
• 24209-38-9 (6R,7R)-7-amino-3-[(1H-1-methyltetrazol-5-yl)thio]methylceph-3-em-4-carboxylic acid 
• 47653-82-7 (6R,7R)-3-((1-methyl-1H-tetrazol-5-ylthio)methyl)-8-oxo-7-(2-phenylacetamido)-5-thia-1-aza-bicyclo [4.2.0]oct-2-ene-2-carboxylic acid 
• 68474-81-7 C₃₁H₂₈N₆O₅S₂ 

Downstream Products

• 68474-81-7 (6R)-3-(1-methyl-1H-tetrazol-5-ylsulfanylmethyl)-5t,8-dioxo-7t-(2-phenyl-acetylamino)-(6rH)-5λ⁴-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid benzhydryl ester 
• 68474-84-0 (6R)-4c-methylsulfanyl-3-(1-methyl-1H-tetrazol-5-ylsulfanylmethyl)-8-oxo-7t-(2-phenyl-acetylamino)-(6rH)-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid 
• 68510-88-3 (6R)-4c-methylsulfanyl-3-(1-methyl-1H-tetrazol-5-ylsulfanylmethyl)-8-oxo-7t-(2-phenyl-acetylamino)-(6rH)-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid benzhydryl ester 
• 68510-85-0 (6R)-4c-methylsulfanyl-3-(1-methyl-1H-tetrazol-5-ylsulfanylmethyl)-5t,8-dioxo-7t-(2-phenyl-acetylamino)-(6rH)-5λ⁴-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid benzhydryl ester 
• 64278-77-9 (6R-cis)-7-methoxy-3-<<(1-methyl-1-H-tetrazol-5-yl)thio>methyl>-8-oxo<(phenylacetyl)amino>-5-thia-1-azabicyclo<4.2.0>oct-2-ene-2-carboxylic acid diphenylmethyl ester 
• 47653-82-7 (6R,7R)-3-((1-methyl-1H-tetrazol-5-ylthio)methyl)-8-oxo-7-(2-phenylacetamido)-5-thia-1-aza-bicyclo [4.2.0]oct-2-ene-2-carboxylic acid 

Relevant academic research and scientific papers

A novel synthetic route to 7-MAC from 7-ACA

An efficient and practical seven-step procedure is described for the synthesis of (6R,7S)-benzhydryl-7-amino-7-methoxy-3-((1-methyl-1H-tetrazol-5-ylthio)methyl)-8-oxo-5-thia-1-aza-bicyclo [4.2.0]oct-2-ene-2-carboxylate (7-MAC, 3) with overall yield of 49?%. This synthesis features a convenient and highly selective method for the introduction of 7α-methoxy group to cephalosporin nucleus in 10 using MeOLi/t-BuOCl in THF.

Synthesis method of methoxy cephalosporin drug intermediate 7-MAC

The invention provides a synthesis method of a methoxy cephalosporin drug intermediate 7alpha-methoxy-7beta-amino-3-(1-methyl-1H-tetrazole-5-methylthio)-3-cephem-4-diphenylmethyl carboxylate (7-MAC). The synthesis method comprises steps as follows: 7-aminocephalosporanic acid (7-ACA) is taken as a raw material, a side chain at a C-3 site and amino at a C-7beta site are modified firstly, oxidative rearrangement and reduction are performed after protection of diphenylmethyl at a C-4 site, a methoxy group is selectively introduced to a C-7alpha site, an amino protecting group is removed finally, and 7-MAC is obtained through 7-step reaction. According to the synthesis method of the methoxy cephalosporin drug intermediate 7-MAC, the defects that byproducts such as methyl mercaptan and the like are required to be removed while the methoxy group is introduced in the existing synthesis technology are overcome. Meanwhile, the synthesis method of the methoxy cephalosporin drug intermediate7-MAC does not adopt diazo compounds, and accordingly, danger such as explosion possibly caused by the diazo compounds is eliminated.