合成路线:The condensation of cyclohexanecarbonyl chloride (I) with 3-fluorobenzyl bromide (II) by means of tetrakis(triphenylphosphine)palladium and Zn in dimethoxyethane gives the ethanone (III),which is treated with lead tetraacetate in acetic acid,yielding the alpha-acetoxyethanone (IV).The cyclization of (IV) with ammonium acetate in refluxing acetic acid affords the oxazole derivative (V),which is treated with chlorosulfonic acid at 100 C,yielding the 4-chlorosulfonyl derivative (VI).Finally,this compound is amidated with ammonia in THF/water.
参考文献标题:JTE-522
文献作者:Silvestre,J.S.; Leeson,P.A.; Castar,J.
参考来源:Drugs Fut 1998,23(6),598
合成路线:The condensation of cyclohexanecarbonyl chloride (I) with 3-fluorobenzyl bromide (II) by means of tetrakis(triphenylphosphine)palladium and Zn in dimethoxyethane gives the ethanone (III),which is treated with lead tetraacetate in acetic acid,yielding the alpha-acetoxyethanone (IV).The cyclization of (IV) with ammonium acetate in refluxing acetic acid affords the oxazole derivative (V),which is treated with chlorosulfonic acid at 100 C,yielding the 4-chlorosulfonyl derivative (VI).Finally,this compound is amidated with ammonia in THF/water.
参考文献标题:4-(4-Cycloalkyl/aryl-oxazol-5-yl)benzenesulfonamides as selective cyclooxygenase-2 inhibitors: Enhancement of the selectivity by introduction of a fluorine atom and identification of a potent,highly selective,and orally active COX-2 inhibitor JTE-522
文献作者:Hashimoto,H.; Imamura,K.; Haruta,J.; Wakitani,K.
参考来源:J Med Chem 2002,45(7),1511
产品链接: CAS No. 180200-68-4››