7-MAC

Base Information

• Chemical Name: 7-MAC
• CAS No.: 56610-72-1
• Molecular Formula: C24H24N6O4S2
• Molecular Weight: 524.624
• Mol file: 56610-72-1.mol

Synonyms:5-Thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylicacid, 7-amino-7-methoxy-3-[[(1-methyl-1H-tetrazol-5-yl)thio]methyl]-8-oxo-,diphenylmethyl ester, (6R-cis)-;Diphenylmethyl 7b-amino-7a-methoxy-3-[[(1-methyl-1H-tetrazol-5-yl)thio]methyl]-3-cephem-4-carboxylate;

Chemical Property of 7-MAC

Chemical Property:

• Appearance/Colour: faint yellow to yellow powder
• Vapor Pressure: 5.89E-22mmHg at 25°C
• Melting Point: 120°C(lit.)
• Refractive Index: 1.733
• Boiling Point: 743.2 °C at 760 mmHg
• PKA: 3.39±0.60(Predicted)
• Flash Point: 403.2 °C
• PSA: 176.06000
• Density: 1.5 g/cm³
• LogP: 2.74380
• Storage Temp.: under inert gas (nitrogen or Argon) at 2–8 °C
• Solubility.: Chloroform (Slightly), Methanol (Slightly, Heated)

Purity/Quality:

99% ^*data from raw suppliers

7β-Amino-7α-methoxy-3-(1-methyl-5-tetrazolylthio)methyl-3-cephem-4-carboxylicAcidDiphenylmethylEster ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Uses: 7-MAC is a 7α-methoxycephalosporin derivative used as an intermediate in the preparation of Cefmetazole (C242850) and other semi-synthetic antibiotics.

Technology Process of 7-MAC

There total 19 articles about 7-MAC which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 94.1%

C31H28N6O5S2 → diphenylmethyl (6R,7S)-7-amino-7-methoxy-3-<<(1-methyl-1H-tetrazol-5-yl)thio>methyl>-Δ3-cephem-4-carboxylate (56610-72-1)

Guidance literature:

With pyridine; bis(trichloromethyl) carbonate; In dichloromethane; at -25 - 5 ℃; for 3h; Reagent/catalyst; Temperature; Solvent; Inert atmosphere;

Reference yield: 91.0%

(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 (64278-77-9) → diphenylmethyl (6R,7S)-7-amino-7-methoxy-3-<<(1-methyl-1H-tetrazol-5-yl)thio>methyl>-Δ3-cephem-4-carboxylate (56610-72-1)

Guidance literature:

With pyridine; phosphorus pentachloride; In methanol; dichloromethane; at -30 - 5 ℃; for 4h; Reagent/catalyst;

Reference yield: 45.0%

(6R,7S)-7-[1-Chloro-but-(E)-ylideneamino]-7-methoxy-3-(1-methyl-1H-tetrazol-5-ylsulfanylmethyl)-8-oxo-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid benzhydryl ester (75072-10-5) → 2-propylbenzo[d]thiazole (17229-76-4) + diphenylmethyl (6R,7S)-7-amino-7-methoxy-3-<<(1-methyl-1H-tetrazol-5-yl)thio>methyl>-Δ3-cephem-4-carboxylate (56610-72-1) + (6R,7S)-7-Butyrylamino-7-methoxy-3-(1-methyl-1H-tetrazol-5-ylsulfanylmethyl)-8-oxo-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid benzhydryl ester (75072-09-2)

Guidance literature:

With pyridine; 2-amino-benzenethiol; In dichloromethane; for 1.5h; Ambient temperature;

DOI:10.1039/c39800000293

upstream raw materials:

(S)-7-[(Z)-2-Chloro-3-phenyl-prop-2-en-(E)-ylideneamino]-7-methoxy-3-(1-methyl-1H-tetrazol-5-ylsulfanylmethyl)-8-oxo-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid benzhydryl ester

(R)-7-Amino-3-(1-methyl-1H-tetrazol-5-ylsulfanylmethyl)-8-oxo-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid benzhydryl ester

(R)-3-(1-Methyl-1H-tetrazol-5-ylsulfanylmethyl)-8-oxo-7-[2,2,3-trichloro-3-phenyl-prop-(E)-ylideneamino]-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid benzhydryl ester

(6R)-7t-(3,5-di-tert-butyl-4-hydroxy-benzylideneamino)-7c-methoxy-3-(1-methyl-1H-tetrazol-5-ylsulfanylmethyl)-8-oxo-(6rH)-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid benzhydryl ester

Downstream raw materials:

Cefmetazole

(6R)-7c-methoxy-3-(1-methyl-1H-tetrazol-5-ylsulfanylmethyl)-8-oxo-7t-((R)-2-thiophen-2-yl-2-ureido-acetylamino)-(6rH)-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid benzhydryl ester

(6R)-7c-methoxy-3-(1-methyl-1H-tetrazol-5-ylsulfanylmethyl)-8-oxo-7t-((S)-2-thiophen-2-yl-2-ureido-acetylamino)-(6rH)-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid benzhydryl ester

(6R)-7c-methoxy-3-(1-methyl-1H-tetrazol-5-ylsulfanylmethyl)-8-oxo-7t-((S)-2-thiophen-2-yl-2-ureido-acetylamino)-(6rH)-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid

Refernces

• 1、 -. "Synthesis method of methoxy cephalosporin drug intermediate 7-MAC". . . Retrieved 2016/10/09.
• 2、 Atsumi,Katano,Nishihata,et al.. "A new synthetic route to 7α-methoxycephalosporins". . p. 2977 - 2980. Retrieved 2007/10/02.