[CH:1]1[C:6](Cl)=[CH:5][C:4]2[NH:8][C:9]([O:11][C:3]=2[CH:2]=1)=[O:10].[C:12]([O:16][C:17]([NH:19][CH2:20][CH:21]=[CH2:22])=[O:18])([CH3:15])([CH3:14])[CH3:13].C1(C)C=CC=CC=1P(C1C=CC=CC=1C)C1C=CC=CC=1C>C([O-])(=O)C.C([O-])(=O)C.[Pd+2].C(#N)C>[C:12]([O:16][C:17]([NH:19][CH2:20][CH:21]=[CH:22][C:6]1[CH:1]=[CH:2][C:3]2[O:11][C:9](=[O:10])[NH:8][C:4]=2[CH:5]=1)=[O:18])([CH3:15])([CH3:14])[CH3:13]A mixture of chlorzoxazone, 3-(t-butoxycarbonylamino)-1-propene, palladium diacetate, tritolylphosphine, and acetonitrile is cooled to −78° C., degassed, and sealed in a reaction tube. The mixture is kept at 50° C. with stirring for 60 hours, then cooled and opened and the acetonitrile removed under vacuum. The residue is dissolved in ethyl acetate and washed successively with 5% aqueous NaHCO3 and brine. After drying over Mg2SO4, the mixture is filtered and evaporated. Silica gel chromatography gives 5-(3-(t-butoxycarbonylamino)-1-propenyl)-2-benzoxazolone.
読み込み中…
