53116-50-0

Usage

Uses

Used in Pharmaceutical Industry:
P-NITROBENZYL 7-PHENYLACETAMINO-3-HYDROXY-3-CEPHEM-4-CARBOXYLATE is used as an antibiotic for treating a wide range of bacterial infections. Its broad-spectrum activity allows it to target both Gram-positive and Gram-negative bacteria, making it a versatile option in combating various microbial infections.
Used in Research and Development:
In the field of microbiology and pharmaceutical research, P-NITROBENZYL 7-PHENYLACETAMINO-3-HYDROXY-3-CEPHEM-4-CARBOXYLATE serves as a valuable compound for studying the mechanisms of action of cephalosporin antibiotics and their potential applications in medicine. Researchers can use P-NITROBENZYL 7-PHENYLACETAMINO-3-HYDROXY-3-CEPHEM-4-CARBOXYLATE to investigate new methods of combating antibiotic resistance and developing more effective treatments for bacterial infections.
Used in Drug Formulation:
P-NITROBENZYL 7-PHENYLACETAMINO-3-HYDROXY-3-CEPHEM-4-CARBOXYLATE can be incorporated into various drug formulations, such as tablets, capsules, injections, or oral suspensions, to provide targeted treatment for bacterial infections. Its stability and bioavailability, enhanced by the p-nitrobenzyl group, make it suitable for different administration routes, ensuring effective delivery of the antibiotic to the site of infection.
Overall, P-NITROBENZYL 7-PHENYLACETAMINO-3-HYDROXY-3-CEPHEM-4-CARBOXYLATE is a promising cephalosporin antibiotic with potential applications in the pharmaceutical industry, research and development, and drug formulation. Its broad-spectrum activity, stability, and bioavailability make it a valuable tool in the fight against bacterial infections.

Synthetic route

C22H19N3O6S → p-nitrobenzyl 7-phenylacetamido-3-hydroxy-3-cephalosporin-4-carboxylate (53116-50-0)

Conditions	Yield
Stage #1: C22H19N3O6S With sodium carbonate; p-toluenesulfonyl chloride In dichloromethane at -5℃; for 2h; Stage #2: With morpholine In dichloromethane for 0.5h; Further stages;	82.7%

(6R)-3-methylene-8-oxo-7t-(2-phenyl-acetylamino)-(6rH)-5-thia-1-aza-bicyclo[4.2.0]octane-2ξ-carboxylic acid 4-nitro-benzyl ester (53116-49-7) → p-nitrobenzyl 7-phenylacetamido-3-hydroxy-3-cephalosporin-4-carboxylate (53116-50-0)

Conditions	Yield
With ozone In dichloromethane

(6R,7R)-3-Methylene-5,8-dioxo-7-phenylacetylamino-5λ4-thia-1-aza-bicyclo[4.2.0]octane-2-carboxylic acid 4-nitro-benzyl ester → p-nitrobenzyl 7-phenylacetamido-3-hydroxy-3-cephalosporin-4-carboxylate (53116-50-0)

Conditions	Yield
With Lawessons reagent; ozone 1.) CH2Cl2, 2.) CH2Cl2; Yield given. Multistep reaction;

p-nitrobenzyl 7-phenylacetamido-3-hydroxy-3-cephalosporin-4-carboxylate (53116-50-0) → C22H19N3O6S

Conditions	Yield
With aluminum (III) chloride; diphenylsilyl chloride In dichloromethane at 15 - 25℃; for 4h;	98.1%

p-nitrobenzyl 7-phenylacetamido-3-hydroxy-3-cephalosporin-4-carboxylate (53116-50-0) → (6R,7R)-7-amino-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid (36923-17-8)

Conditions	Yield
Multi-step reaction with 3 steps 1.1: diphenylsilyl chloride; aluminum (III) chloride / dichloromethane / 4 h / 15 - 25 °C 2.1: diisooctyl phenyl phosphite; bromine; 1H-imidazole / dichloromethane / 5 h / -45 - -40 °C 2.2: 0.5 h 3.1: trimethylsilyl bromide / dichloromethane / 5.5 h / 20 - 25 °C View Scheme

p-nitrobenzyl 7-phenylacetamido-3-hydroxy-3-cephalosporin-4-carboxylate (53116-50-0) → C14H13N3O5S*ClH

Conditions	Yield
Multi-step reaction with 2 steps 1.1: diphenylsilyl chloride; aluminum (III) chloride / dichloromethane / 4 h / 15 - 25 °C 2.1: diisooctyl phenyl phosphite; bromine; 1H-imidazole / dichloromethane / 5 h / -45 - -40 °C 2.2: 0.5 h View Scheme

Upstream product

• 53116-49-7 (6R)-3-methylene-8-oxo-7t-(2-phenyl-acetylamino)-(6rH)-5-thia-1-aza-bicyclo[4.2.0]octane-2ξ-carboxylic acid 4-nitro-benzyl ester 

Downstream Products

• 36923-17-8 (6R,7R)-7-amino-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid 

Relevant academic research and scientific papers

Method for preparing 7-phenylacetylamino-3-hydroxyl-3-cyclo-4-p-nitrobenzyl cephalosporin carboxylate

The invention belongs to the field of preparation methods for compounds and particularly relates to a method for preparing 7-phenylacetylamino-3-hydroxyl-3-cyclo-4-p-nitrobenzyl cephalosporin carboxylate. The 7-phenylacetylamino-3-hydroxyl-3-cyclo-4-p-nitrobenzyl cephalosporin carboxylate is prepared from thiazoline enol ester, which serves as a raw material, by a one-pot method through acylation, ene-amination, bromization and cyclization. According to the method, through one-pot method continuous reactions, the operation is simple, the total reaction time is shortened, and the energy consumption is greatly lowered; and the reaction process is carried out at normal temperature or under the condition of being close to room temperature, the reaction conditions are mild, the reaction time is relatively short, the raw materials used are readily available, the cost is low, the pollution is light, the total yield reaches 82.5% or more, the purity can reach 98.0% or more, and the quality of the product is relatively good, so that the method is applicable to industrial production.

An efficient method for the reduction of cephalosporin sulfoxides

An efficient and convenient method for the reduction of cephalosporin sulfoxides to their corresponding sulfides by Lawesson reagent is reported.