58233-18-4

Basic information

• Product Name: (6R-trans)-3-(acetoxymethyl)-7-[(2-aminothiazol-4-yl)acetamido]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid
• Synonyms: (6R-trans)-3-(acetoxymethyl)-7-[(2-aminothiazol-4-yl)acetamido]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid;RU 7-23345;(6R)-3-(Acetyloxymethyl)-7α-[2-aminothiazol-4-yl(acetyl)amino]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid;(6R-trans)-3-(Acetoxymethyl)-7-((2-aminothiazol-4-yl)acetamido)-8-oxo-5-thia-1-azabicyclo(4.2.0)oct-2-ene-2-carboxylic acid;Einecs 261-175-9;Cefotiam Impurity 8
• CAS NO: 58233-18-4
• Molecular Formula: C₁₅H₁₆N₄O₆S₂
• Molecular Weight: 412.44074
• EINECS: 261-175-9
• Mol File: 58233-18-4.mol
• Article Data: 4

Chemical Properties

• Boiling Point: 846.2°Cat760mmHg
• Flash Point: 465.5°C
• Appearance: /
• Density: 1.65g/cm³
• Vapor Pressure: 1.97E-30mmHg at 25°C
• Refractive Index: 1.703
• PKA: 2.67±0.50(Predicted)
• CAS DataBase Reference: (6R-trans)-3-(acetoxymethyl)-7-[(2-aminothiazol-4-yl)acetamido]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid(CAS DataBase Reference)
• NIST Chemistry Reference: (6R-trans)-3-(acetoxymethyl)-7-[(2-aminothiazol-4-yl)acetamido]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid(58233-18-4)
• EPA Substance Registry System: (6R-trans)-3-(acetoxymethyl)-7-[(2-aminothiazol-4-yl)acetamido]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid(58233-18-4)

Safety Data

• Hazardous Substances Data: 58233-18-4(Hazardous Substances Data)

Usage

Description

(6R-trans)-3-(acetoxymethyl)-7-[(2-aminothiazol-4-yl)acetamido]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid is a complex organic compound with a unique chemical structure. It is characterized by its thiazolyl and acetamido functional groups, which contribute to its potential applications in various fields.

Uses

Used in Pharmaceutical Industry:
(6R-trans)-3-(acetoxymethyl)-7-[(2-aminothiazol-4-yl)acetamido]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid is used as an impurity in the production of Cefotiam, a semi-synthetic cephalosporin antibiotic. Its presence in the manufacturing process may affect the purity and efficacy of the final product, making it an important compound to monitor and control during the synthesis of Cefotiam.

InChI:InChI=1/C15H16N4O6S2/c1-6(20)25-3-7-4-26-13-10(12(22)19(13)11(7)14(23)24)18-9(21)2-8-5-27-15(16)17-8/h5,10,13H,2-4H2,1H3,(H2,16,17)(H,18,21)(H,23,24)

Upstream product

• 64220-26-4 [2-[(triphenyl-methyl)-amino]-thiazol-4-yl] acetic acid 
• 957-68-6 7-Aminocephalosporanic acid 
• 66659-20-9 2-(2-aminothiazol-4-yl)acetic acid hydrochloride 
• 53266-94-7 ethyl 2-amino-1,3-thiazol-4-acetate 
• 58684-54-1 7-(γ-chloroacetoacetamido)cephalosporanic acid 
• 17356-08-0 thiourea 

Downstream Products

• 775233-43-7 (6R)-7t-[2-(2-amino-thiazol-4-yl)-acetylamino]-3-hydroxymethyl-8-oxo-(6rH)-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid 

Relevant articles and documents

Preparation method suitable for industrial production for high-yield high-quality cefotiam hydrochloride

The invention relates to a preparation method suitable for industrial production for high-yield high-quality cefotiam hydrochloride. The method comprises the following steps that (1), methylene dichloride is taken as a solvent, a one-pot method is adopted, ATA,HCl and methylsulfonyl chloride generate a first intermediate in the form of acid anhydride, and then the acid anhydride liquid directly reacts with 7-aminocephalosporanic acid (7-ACA) to generate a second intermediate under the catalysis of organic alkali; (2) acetonitrile is taken as a solvent, the second intermediate reacts with 1-(2-dimethylamine ethyl)-5-sulfydryl-1,2,3,4-tetramidazole (DMMT) in the presence of boron trifluoride acetonitrile complex to obtain crude cefotiam hydrochloride, and then the cefotiam hydrochloride is obtained through rectification. The high-yield high-quality preparation method suitable for the industrial production for the cefotiam hydrochloride has the advantages that the first intermediate and the second intermediate are synthesized, and signal solvents are used separately when the crude cefotiam hydrochloride and the finished cefotiam hydrochloride are prepared so as to facilitate recycle and reuse; the steps are simple in operation, the product conversion rate is high, the impurities are small, the production cost is low, and the method is suitable for the industrial production of thehigh-quality cefotiam hydrochloride.

A new cephalosporin. SCE-963: 7-[2-(2-aminothiazol-4-yl)-acetamido]-3- [[[1-(2-dimethylaminoethyl)-1h-tetrazol-5-yl]-thio]methyl]ceph-3-em-4-carboxylic acid. Chemistry and structure-activity relationships

The synthesis and the in vitro and in vivo antimicrobial activities of a series of 7-[2-(2-aminothiazol-4-yl)acetamido]cephalosporins (1) having varied 3-substituents, such as methyl, hydroxymethyl, acetoxymethyl, pyridiniomethyl and heterocyclicthiomethyls, are described. The derivates having five membered heterocyclicthiomethyls exhibited strong inhibitory activities against Gram-negative organisms including some strains od Escherichia coli and Proteus morganii which are insensitive to cefazolin and cephaloridine. Pronounced activities were noted with 7-[2-(2-aminothiazol-4-yl)-acetamido]-3-[[[1-(2-dimethylaminoethyl)-1H-tetra zol-5-yl]thio]methyl]ceph-3-em-4-carboxylic acid (1y;SCE-963).