English Synonyms
Bextra;valdecoxib;4-(5-Methyl-3-Phenyl-4-Isoxazolyl)benzenesulfonamide;akos 92130;bextra(Valdecoxib);parecoxib Sodium-7;valdecoxib - Sc 65872 | Bextra;parecoxib Sodium Intermediate
Valdecoxib Properties
| Melting point | 162-164°C |
| Boiling Point | 481.2±55.0 °C(Predicted) |
| Density | 1.303±0.06 g/cm3(Predicted) |
| Storage conditions | room temp |
| Solubility | Dimethyl sulfoxide: >25 mg/mL |
| Acidity coefficient (pKa) | 9.83±0.10(Predicted) |
| Form | powder |
| Color | White to off-white |
| InChI | InChI=1S/C16H14N2O3S/c1-11-15(12-7-9-14(10-8-12)22(17,19)20)16(18-21-11)13-5-3-2-4-6-13/h2-10H,1H3,(H2,17,19,20) |
| InChIKey | LNPDTQAFDNKSHK-UHFFFAOYSA-N |
| SMILES | C1(S(N)(=O)=O)=CC=C(C2=C(C)ON=C2C2=CC=CC=C2)C=C1 |
Preparation
1) in a Nitrogen-Protected Flask, 58g of Acetone and 78.1g of Pyrrolidine Were Dissolved in 500ml of Benzene in Turn, Heated to Reflux at 125°c for 1 Hour, And Then Rotary Evaporated to Remove Benzene;
2) 30.6g of Phosphorus Oxychloride Was Dissolved in 200ml of Triethylamine, And Then 119.3g of Chloroform Was Slowly Added Under Ice Bath Conditions to Form a Mixed Solution, And the Above Mixed Solution, 207g of 1-Nitroethylbenzene, And 400ml of Triethylamine Were Added to Step S1 in Turn, Stirred Under Ice Bath Conditions for 1 Hour, And Then the Ice Bath Was Removed, The Temperature Was Raised to 25°c, 256.8g of P-Toluenesulfonamide Was Added, And Stirring Was Continued for 5 Hours to Form a Reaction Solution;
3) the Reaction Solution Was Poured into a Separatory Funnel, Washed with 1l of Water, And Then the Chloroform Layer Was Washed with 6n Hydrochloric Acid, And Finally Washed with 5% Sodium Hydroxide Aqueous Solution;
4) Drying with Anhydrous Magnesium Sulfate and Filtering; and
5) the Solvent Was Removed by a Rotary Evaporator, And the Product Was Distilled Under Vacuum to Obtain the Said Dacoxib. The Obtained Dalicoxib Had a Mass of 302.18 G, A Purity of 99.538%, And a Yield of 95.7%.
Application
Valdecoxib Is Not Only the Key Intermediate in the Synthesis of Parecoxib Sodium, But Also Its Main Hydrolysis Product, And Is the Main Impurity in the Inspection of Related Substances of Parecoxib Sodium.
Application
For the Preparation of Parecoxib: 3.1g (10mmol) of Valdecoxib, 3g (30mmol) of Triethylamine and 3.3g (25mmol) of Propionic Anhydride Are Mixed in Dichloromethane at 20℃ for Reaction. After the Reaction, Pour into Water, Extract with Dichloromethane, Concentrate, Dissolve in Ethanol, Crystallize at 5-10℃, Filter, And Dry to Obtain 3.4g of Parecoxib, With a Yield of 92.4% and a Purity of 99.81%.
Main Uses
Valdecoxib Is Used to Synthesize the Raw Material of Parecoxib Sodium.
Biological Activity
Valdecoxib Is a Potent and Selective Cox-2 Inhibitor with an Ic50 of 5nm.
