82549-51-7

Usage

Uses

Used in Pharmaceutical Industry:
(6R,7R)-7-Amino-3-[(5-methyl-2H-tetrazol-2-yl)methyl]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid is used as an impurity in Cefoperazone (C242900), a second-generation cephalosporin antibiotic. It plays a role in the development and production of antibacterial medications, contributing to the fight against bacterial infections.
As an impurity in Cefoperazone, (6R,7R)-7-Amino-3-[(5-methyl-2H-tetrazol-2-yl)methyl]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid is relevant to the pharmaceutical industry for the following reasons:
1. Quality Control: The presence of (6R,7R)-7-Amino-3-[(5-methyl-2H-tetrazol-2-yl)methyl]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid in Cefoperazone is monitored to ensure the quality and purity of the antibiotic, which is crucial for its effectiveness and safety.
2. Regulatory Compliance: Regulatory agencies require the identification and control of impurities in pharmaceutical products to ensure they meet safety and efficacy standards.
3. Research and Development: Understanding the properties and effects of this impurity can aid in the development of new antibiotics or improvements to existing ones, potentially enhancing their therapeutic benefits and reducing side effects.

Upstream product

• 4076-36-2 5-methyl-1,2,3,4-tetrazole 
• 957-68-6 7-Aminocephalosporanic acid 

Downstream Products

• 82547-58-8 cefteram 
• 82547-81-7 cefteram pivoxil 

Relevant academic research and scientific papers

Preparation method of cefteram pivoxil

The invention relates to a preparation method of cefteram pivoxil. The preparation method comprises following steps: taking 7-ACA and 5-methyltetrazole as starting raw materials, carrying out reactions in the presence of H2SO4 to generate 7-MTCA, protecting the amino groups of aminothiazol acetate, reacting aminothiazol acetate with 7-MTCA under the catalytic effect of AlMe3 to generate an intermediate (I); carrying out esterification reactions between the intermediate (I) and iodomethyl pivalate under the action of a phase transfer catalyst and an acid adsorbent, and removing the amino protection to obtain the target product (cefteram pivoxil). The reaction conditions are mild, the product purity and yield are high, and the technology is stable, is easy for amplification, and is suitablefor industrial production.

Preparation method of cefteram pivoxil

The invention relates to a preparation method of cefteram pivoxil. The method comprises the following steps: by using 7-ACA as a raw material, carrying out reaction on the 7-ACA and 5-methyltetrazole under the catalytic action of a BF3 tetrahydrofuran complex to obtain the 7-MTCA; carrying out reaction on the 7-MTCA and AE active ester to obtain cefteram acid; preparing a cefteram sodium salt from the cefteram acid; and carrying out esterification reaction on the refined sodium salt and iodomethyl pivalate to obtain the cefteram pivoxil. The method is simple to operate and mild in reaction conditions. The prepared product has the advantages of low impurity content and high yield, and is beneficial to industrial production.