新产品编号:668113
Chemical Name: Phosphoric acid 2-methoxy-5-(2,3,4,5,6-pentafluorophenylsulfonamido)phenyl mono ester; 2,3,4,5,6-Pentafluoro-N-[4-methoxy-3-(phosphonooxy)phenyl]benzenesulfonamide
CAS No. 253141-29-6
项目整合开发状态: Preclinical
项目研究机构: Amgen (Originator)
合成路线:The condensation of 2(R)-(2,2-dimethyl-5-oxo-1,3-dioxolan-4(S)-yl)-4,4-dimethylpentanoic acid (I) with 2,2-dimethylpropanal (II),ter-butyl isocyanide (III) and ammonia in methanol gives the intermediate (IV),which,without isolation is treated with hydroxylamine to yield the target compound as a mixture of diastereomers.
合成路线:The title sulfonamide was obtained by condensation of pentafluorophenyl sulfonyl chloride (I) with 3-hydroxy-4-methoxyaniline (II) in the presence of pyridine.
合成路线:Condensation of pentafluorophenyl sulfonyl chloride (I) with 3-hydroxy-4-methoxyaniline (II) in the presence of pyridine afforded sulfonamide (III).Treatment of (III) with N,N-diisopropyl dibenzylphosphoramidite (A) and tetrazole gave phosphite ester (IV),which was subsequently oxidized to phosphate (V) by means of tert-butyl peroxide.Finally,hydrogenolysis of the benzyl phosphate ester groups of (V) in the presence of Pd/C and 1,4-cyclohexadiene furnished the title compound.
📌 参考资料/链接：
参考文献标题:Pentafluorobenzenesulfonamides and analogs
文献作者:Flygare,J.; Medina,J.; Shan,B.; Clark,D.; Rosen,T.(Tularik Inc.)
参考来源:EP 0939627; WO 9805315
📄 详细内容
合成路线:By condensation of pentafluorophenylsulfonyl chloride (I) with 3-fluoro-4-methoxyaniline (II) in pyridine.
合成路线:The title sulfonamide was obtained by condensation of pentafluorophenyl sulfonyl chloride (I) with 3-hydroxy-4-methoxyaniline (II) in the presence of pyridine.
合成路线:Condensation of pentafluorophenyl sulfonyl chloride (I) with 3-hydroxy-4-methoxyaniline (II) in the presence of pyridine afforded sulfonamide (III).Treatment of (III) with N,N-diisopropyl dibenzylphosphoramidite (A) and tetrazole gave phosphite ester (IV),which was subsequently oxidized to phosphate (V) by means of tert-butyl peroxide.Finally,hydrogenolysis of the benzyl phosphate ester groups of (V) in the presence of Pd/C and 1,4-cyclohexadiene furnished the title compound.
参考文献标题:Pentafluorobenzenesulfonamides and analogs
文献作者:Rosen,T.; Medina,J.C.; Flygare,J.; Shan,B.; Clark,D.(Tularik Inc.)
参考来源:EP 0896533; JP 2000505459; US 5880151; WO 9730677
合成路线:Condensation of pentafluorophenyl sulfonyl chloride (I) with 3-hydroxy-4-methoxyaniline (II) in the presence of pyridine afforded sulfonamide (III).Treatment of (III) with N,N-diisopropyl dibenzylphosphoramidite (A) and tetrazole gave phosphite ester (IV),which was subsequently oxidized to phosphate (V) by means of tert-butyl peroxide.Finally,hydrogenolysis of the benzyl phosphate ester groups of (V) in the presence of Pd/C and 1,4-cyclohexadiene furnished the title compound.
参考文献标题:Arylsulfonanilide phosphates
文献作者:Houze,J.B.(Tularik Inc.)
参考来源:WO 9967258