Methyl chloroformate → 3,3a,4,5-tetrahydro-3a-methoxycarbonyl-N-[4'-(trifluoromethyl)phenyl]-2H-benz[g]indazole-2-carboxamide
反応式
C(NC(C)C)(C)C.C([Li])CCC.[F:13][C:14]([F:38])([F:37])[C:15]1[CH:20]=[CH:19][C:18]([NH:21][C:22]([N:24]2[CH2:32][CH:31]3[C:26]([C:27]4[CH:36]=[CH:35][CH:34]=[CH:33][C:28]=4[CH2:29][CH2:30]3)=[N:25]2)=[O:23])=[CH:17][CH:16]=1.Cl[C:40]([O:42][CH3:43])=[O:41]>C1COCC1.CCCCCC>[CH3:43][O:42][C:40]([C:31]12[CH2:30][CH2:29][C:28]3[CH:33]=[CH:34][CH:35]=[CH:36][C:27]=3[C:26]1=[N:25][N:24]([C:22]([NH:21][C:18]1[CH:17]=[CH:16][C:15]([C:14]([F:13])([F:37])[F:38])=[CH:20][CH:19]=1)=[O:23])[CH2:32]2)=[O:41]参加物
反応物 4
生成物 1
試薬・触媒・溶媒 2
反応条件
- 温度
- 0 °C
実験手順
To a solution of 0.9 ml of diisopropylamine in 10 ml of THF, at -78° C., was added 2.3 ml of 2.5M n-butyl lithium in hexane and the mixture was stirred for 5 mins. To this solution was added a solution of 1.0 g of the title compound of Step A in 5 ml of THF. The reaction was warmed to 0° C., recooled to -78° C. and then 0.75 ml of methyl chloroformate was added. The reaction mixture was then stirred for 24 h, with gradual warming to room temperature, quenched with 0.5 ml of glacial acetic acid, and poured into a 5% solution of aqueous NaHCO3. The mixture was extracted with chloroform, dried over magnesium sulfate and concentrated. Chromatography on silica gel with 30% ethyl acetate hexane afforded 0.25 g of the title compound, m.p. 177° to 180° C.
後処理
- customrecooled to -78° C.
- stirringThe reaction mixture was then stirred for 24 h
- temperaturewith gradual warming to room temperature
- customquenched with 0.5 ml of glacial acetic acid
- additionpoured into a 5% solution of aqueous NaHCO3
- extractionThe mixture was extracted with chloroform
- dry with materialdried over magnesium sulfate
- concentrationconcentrated
出典と根拠
- ORDレコード
- ord-e5ea415d48054ca5aae5b4caae1d1dd0
- 出典データセット
- uspto-grants-1997_01
- 特許番号
- US05591764
反応ノート
読み込み中…