反応式
[CH3:1][N:2]1[C@H:11]2[C@@:6]([CH3:17])([C:7]3[CH:15]=[CH:14][C:13]([SH:16])=[CH:12][C:8]=3[CH2:9][CH2:10]2)[CH2:5][CH2:4][C:3]1=[O:18].C(=O)([O-])[O-].[K+].[K+].Cl[C:26]1[S:27][C:28]2[CH:34]=[CH:33][CH:32]=[C:31]([F:35])[C:29]=2[N:30]=1.CN(C)C=O>C(OCC)(=O)C>[CH3:1][N:2]1[C@H:11]2[C@@:6]([CH3:17])([C:7]3[CH:15]=[CH:14][C:13]([S:16][C:26]4[S:27][C:28]5[CH:34]=[CH:33][CH:32]=[C:31]([F:35])[C:29]=5[N:30]=4)=[CH:12][C:8]=3[CH2:9][CH2:10]2)[CH2:5][CH2:4][C:3]1=[O:18]参加物
反応物 4
生成物 1
試薬・触媒・溶媒 1
実験手順
A 15 mL round bottom flask was charged with (+)-(4aR)-(10bR)-4-methyl-8-mercapto-10b-methyl-1,2,3,4,4a,5,6,10b-octahydrobenzo[f]quinolin-3-one (100 mg, 0.38 mmol), potassium carbonate (158 mg, 1.14 mmol), 2-chloro-4-fluoro benzothiazole (86 mg, 0.46 mmol and 1 mL of anhydrous dimethylformamide, fitted with a reflux condenser, and the stirred mixture was heated at 60°, under nitrogen, for 48 h. The mixture was cooled, diluted with ethyl acetate (75 mL) and washed with brine (2×25 mL). The combined organic extracts were dried over sodium sulfate, concentrated, and purified by silica gel chromatography (80% ethyl acetate/hexanes eluent) to give 91 mg (58%) of the title compound as an amorphous solid. mp 140°-145°. FDMS: m/e=412. α[D]589 =+70.06 (c=0.52, chloroform).
後処理
- customfitted with a reflux condenser
- temperaturethe stirred mixture was heated at 60°, under nitrogen, for 48 h
- temperatureThe mixture was cooled
- washwashed with brine (2×25 mL)
- dry with materialThe combined organic extracts were dried over sodium sulfate
- concentrationconcentrated
- custompurified by silica gel chromatography (80% ethyl acetate/hexanes eluent)
出典と根拠
- ORDレコード
- ord-8b744f628d54455aa6639f56a3674fa0
- 出典データセット
- uspto-grants-1997_05
- 特許番号
- US05629007
関連ノート
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