Parecoxib sodium, SC-69124A, Rayzon, Xapit, Dynastat

合成路线:The acylation of 4-(5-methyl-3-phenylisoxazol-4-yl)benzenesulfonamide,valdecoxib (I),with propionic anhydride (II) by means of TEA and DMAP in THF gives N-[4-(5-methyl-3-phenylisoxazol-4-yl)phenylsulfonyl]propionamide (III),which is then treated with NaOH in ethanol.

参考文献标题:N-[[(5-Methyl-3-phenylisoxazol-4-yl)-phenyl]sulfonyl]propanamide,sodium salt,parecoxib sodium: A potent and selective inhibitor of COX-2 for parenteral administration
文献作者:Talley,J.J.; Bertenshaw,S.R.; Brown,D.L.; Carter,J.S.; Graneto,M.J.; Kellog,M.S.; Koboldt,C.M.; Yuan,J.; Zhang,Y.Y.; Seibert,K.
参考来源:J Med Chem 2000,43(9),1661


合成路线:Deoxybenzoin (I) is converted to the corresponding oxime (II) by treatment with NH2OH稨Cl under basic conditions either with sodium acetate in aqueous ethanol or in toluene in presence of potassium hydroxide in absolute ethanol.Deprotonation of the oxime under nitrogen with 2eq of butyllithium in THF followed by cyclization in ethyl acetate or acetic anhydride affords isoxazoline (III).Finally,treatment of (III) with cold chlorosulfonic acid followed by reaction of the intermediate sulfonyl chloride with aqueous ammonia affords the desired product.

合成路线:The acylation of 4-(5-methyl-3-phenylisoxazol-4-yl)benzenesulfonamide,valdecoxib (I),with propionic anhydride (II) by means of TEA and DMAP in THF gives N-[4-(5-methyl-3-phenylisoxazol-4-yl)phenylsulfonyl]propionamide (III),which is then treated with NaOH in ethanol.
参考文献标题:Valdecoxib and Parecoxib Sodium
文献作者:Leeson,P.; Castar,J.; Castar,R.M.; Sorbera,L.A.
参考来源:Drugs Fut 2001,26(2),133