181696-35-5

Basic information

• Product Name: Valdecoxib IMpurity D
• Synonyms: 4-(5-Methyl-3-phenyl-4-isoxazolyl)benzenesulfonic Acid;Valdecoxib IMpurity D;Valdecoxib Sulfonic Acid;4-(5-Methyl-3-phenylisoxazol-4-yl)benzenesulfonic acid;Valdecoxib IMpurity-D (Valdecoxib SulfonicAcid);Benzenesulfonic acid, 4-(5-Methyl-3-phenyl-4-isoxazolyl)-;3-Phenyl-4-(4-aMinosulfonylbenzyl)-5-Methylisoxazole ,Valdecoxib Sulfonyl Chloride ,valdecoxib iMpurity D
• CAS NO: 181696-35-5
• Molecular Formula: C₁₆H₁₃NO₄S
• Molecular Weight: 315.34372
• Mol File: 181696-35-5.mol
• Article Data: 8

Chemical Properties

• Appearance: /
• Density: 1.341±0.06 g/cm3(Predicted)
• Storage Temp.: Sealed in dry,Room Temperature
• Solubility: Acetone (Slightly), DMSO (Slightly), Ethyl Acetate (Slightly), Methanol (Slightl
• PKA: -0.92±0.50(Predicted)
• CAS DataBase Reference: Valdecoxib IMpurity D(CAS DataBase Reference)
• NIST Chemistry Reference: Valdecoxib IMpurity D(181696-35-5)
• EPA Substance Registry System: Valdecoxib IMpurity D(181696-35-5)

Safety Data

• Hazardous Substances Data: 181696-35-5(Hazardous Substances Data)

Usage

Uses

Valdecoxib Sulfonic Acid is a metabolite of the potent and specific inhibitor of cyclooxygenase-2, Valdecoxib (V090000).

Upstream product

• 932-90-1 Benzaldoxime 
• 509074-26-4 4-(5-methyl-3-phenylisoxazol-4-yl)benzenesulfonyl chloride 
• 103-79-7 1-phenyl-acetone 
• 52201-28-2 1-(1-methyl-2-phenyl ethenyl)-pyrrolidine 
• 857259-65-5 5-methyl-3,4-diphenyl-5-(pyrrolidin-1-yl)-4,5-dihydroisoxazole 
• 37928-17-9 5-methyl-3,4-diphenyl isoxazole 

Downstream Products

• 897927-43-4 4-[(5-methyl-3-phenyl)-4-isoxazolyl]benzenesulfonate sodium salt 
• 181695-72-7 valdecoxib 

Relevant articles and documents

Preparation method of parecoxib sodium

The invention belongs to the technical field of drug preparation, and specifically relates to a preparation method of parecoxib sodium. The preparation method comprises sulfonation reactions, amination reactions, propionylation reactions, and salt forming reactions. In sulfonation reactions, 5-methyl-3,4-diphenyl isoxazole is taken as the primary raw material and directly carries out reactions with chlorosulfonic acid, after reactions, and the reaction system is poured into water to carry out quenching to obtain suspension of reaction products. All used reagents are common reagents; the preparation method only uses third kind solvents, which are regulated by International Council for Harmonization (ICH) and are harmless for human body; the operation of the preparation method and post treatment is simple, the repeatability is good, the yield is high, and the cost is low. The purity of prepared parecoxib sodium can reach 99.9% or more. The quality of prepared parecoxib sodium is higher than the standards made by a plant that develops parecoxib sodium. The preparation method is suitable for industrial production of pharmaceutical enterprises.

Method for preparing cyclooxygenase-2 inhibitor parecoxib

The invention discloses a method for preparing a cyclooxygenase-2 inhibitor parecoxib. The method comprises the following steps: 1) enabling benzaldoxime and 1-(4-sulfonyl phenyl)propyne to react in an illumination condition in the presence of tri(2-phenylpyridine)iridium (III), triethylamine and magnesium oxide to obtain 5-methyl-3-phenyl-4-(4-sulfonyl phenyl)isoxazole; 2) conducting a contact reaction between 5-methyl-3-phenyl-4-(4-sulfonyl phenyl)isoxazole obtained in the step 1) and thionyl chloride; after the reaction, extracting dichloromethane; directly adding the dichloromethane phase into ammonia water; separating organic phase; washing and concentrating; and recrystallizing with ethanol to obtain valdecoxib; and 3) enabling the valdecoxib obtained in the step 2) to react with propionic anhydride in the presence of triethylamine to obtain parecoxib. The parecoxib preparation method disclosed by the invention has the advantages of simple steps, high yield and simple aftertreatment.

Application of [3+2]-cycloaddition in the synthesis of valdecoxib

A large scale synthesis of valdecoxib 1 is described. Our work features potential application of [3+2]-dipolar cycloaddition involving enamine and in situ-generated nitrile oxide derivatives. Dr. Reddy's Laboratories Ltd.