[N:1]1([C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])[CH2:6][CH2:5][NH:4][CH2:3][CH:2]1[C:7]([O:9][CH3:10])=[O:8].[CH:18]1[CH:23]=[CH:22][C:21]([CH2:24]Br)=[CH:20][CH:19]=1.C(N(CC)CC)C>C(#N)C>[CH2:24]([N:4]1[CH2:5][CH2:6][N:1]([C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])[CH:2]([C:7]([O:9][CH3:10])=[O:8])[CH2:3]1)[C:21]1[CH:22]=[CH:23][CH:18]=[CH:19][CH:20]=1To a dry 100 ml one necked round bottom flask equipped with a stirring bar was added 1-tert-butyl 2-methyl piperazine-1,2-dicarboxylate (5 g, 20.5 mmol) under N2 (FIG. 1). Anhydrous acetonitrile (60 mL) was added followed by the additions of BnBr (2.7 mL, 22.5 mmol) and triethylamine (8.5 ml, 61.5 mmol). A condenser was then put on to the flask and the reaction mixture was heated at 71° C. for 45 minutes. The reaction mixture was allowed to come to room temperature and concentrated under reduced pressure. It was then diluted with dicholoromethane and washed with water and brine. The organic layer was dried over Na2SO4, filtered and concentrated under reduced pressure. The crude compound was purified with flash column (PE:EA=8:1) to yield 4.5 g (66%) of 111a. MS: [M+H]+: 335
読み込み中…
