89495-46-5

Basic information

• Product Name: S-Cefotetan
• Synonyms: 5-Thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid, 7-[[[4-(2-amino-1-carboxy-2-oxoethylidene)-1,3-dithietan-2-yl]carbonyl]amino]-7-methoxy-3-[[(1-methyl-1H-tetrazol-5-yl)thio]methyl]-8-oxo-, [6R-[6α,7α,7(S*)]]-;S-Cefotetan
• CAS NO: 89495-46-5
• Molecular Formula: C₁₇H₁₇N₇O₈S₄
• Molecular Weight: 575.6
• Mol File: 89495-46-5.mol

Chemical Properties

• Appearance: /
• CAS DataBase Reference: S-Cefotetan(CAS DataBase Reference)
• NIST Chemistry Reference: S-Cefotetan(89495-46-5)
• EPA Substance Registry System: S-Cefotetan(89495-46-5)

Safety Data

• Hazardous Substances Data: 89495-46-5(Hazardous Substances Data)

Upstream product

• 61807-78-1 7β-bromoacetamido-7α-methoxy-3-(1-methyltetrazol-5-yl)thiomethyl-Δ³-cephem-4-carboxylic acid 
• 76857-14-2 4-carboxy-5-mercapto-3-hydroxy-isothiazolium trisodium 
• 69712-30-7 7β-(4-carboxy-3-hydroxyisothiazol-5-yl)thioacetamido-7α-methoxy-3-(1-methyltetrazol-5-yl)thiomethyl-Δ³-cephem-4-carboxylic acid 
• 79072-74-5 cefotetan disodium salt 
• 56610-72-1 diphenylmethyl (6R,7S)-7-amino-7-methoxy-3-<<(1-methyl-1H-tetrazol-5-yl)thio>methyl>-Δ³-cephem-4-carboxylate 

Relevant articles and documents

New crystal of cefotetan acid and preparation method thereof

The invention relates to a new crystal of cefotetan acid and a preparation method thereof. The invention provides a new crystal form of [6R-(6a,7alpha)]-7-[[[4-(2-amino-1-carboxyl-2-oxoethylidene)-1,3-dithioheterocyclobutyl -2-yl]carbonyl]amino]-7-methoxy-3-[[(1-methyl-1H-tetrazolyl-5-yl)thio]methyl]-8-oxo-5-thia-1-azabicyclo[4,2,0]octyl-2-ene-2-formic acid. The crystal form has characteristic peaks when the reflection angle 2theta in the X-ray powder diffractogram is 11.66+/-0.1 degrees, 17.53+/-0.1 degrees, 17.72+/-0.1 degrees, 18.91+/-0.1 degrees, 20.01+/-0.1 degrees, 21.02+/-0.1 degrees, 22.24+/-0.1 degrees and 23.33+/-0.1 degrees. The compound crystal form has the advantages of favorable stability, simple preparation technique and lower preparation cost, and can implement industrial production.

Acid cefotetan totally solvent-free and method for obtaining same

The invention relates to a method for obtaining cefotetan acid substantially free of tautomer, by initial isolation of the crude product with a limited tautomer content, followed by purification through a chromatographic column. The invention also concerns the acid cefotetan totally solvent-free thereby obtained.

Acid cefotetan totally solvent free and method for obtaining same

The invention relates to a method for obtaining cefotetan acid substantially free of tautomer, by initial isolation of the crude product with a limited tautomer content, followed by purification through a chromatographic column. The invention also concerns the acid cefotetan totally free from solvents thereby obtained.

PROCESS FOR OBTAINING CEFOTETAN WITH HIGH YIELD

The invention relates to a method for obtaining cefotetan acid substantially free of tautomer, by treating crude cefotetan with Al3+ ions which cause the tautomer to precipitate. The precipitate is eliminated by filtration to provide a solution from which practically tautomer-free cefotetan is obtained.

Process for the preparation of cefotetan

The invention relates to a method for obtaining cefotetan acid substantially free of tautomer, by treating crude cefotetan with Al3+ ions which cause the tautomer to precipitate. The precipitate is eliminated by filtration to provide a solution from which practically tautomer-free cefotetan is obtained.

Process development and pilot-scale synthesis of cefotetan

Strategies that were adopted during the process development of Cefotetan in order to achieve a cost-effective commercial-scale synthesis are described herein. These included replacement of the trifluoroacetic acid used for cleavage of the benzhydryl ester and the development of an alternative synthetic route. This work led to improvement of both the impurity profile and the yield of the process. The pilot-scale synthesis of Cefotetan is described in detail in the Experimental Section. The scaled-up process has been successfully used for the commercial manufacture of Cefotetan since 1983.