反応式
[CH:1]1[C:6]2[C:7](=[O:16])[NH:8][C:9]3[CH:15]=[CH:14][CH:13]=[CH:12][C:10]=3[S:11][C:5]=2[CH:4]=[CH:3][CH:2]=1.[H-].[Na+].Br[CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][C:26]([O:28][CH2:29][CH3:30])=[O:27]>CN(C=O)C>[O:16]=[C:7]1[C:6]2[CH:1]=[CH:2][CH:3]=[CH:4][C:5]=2[S:11][C:10]2[CH:12]=[CH:13][CH:14]=[CH:15][C:9]=2[N:8]1[CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][C:26]([O:28][CH2:29][CH3:30])=[O:27]参加物
5
反応条件
- 温度
- 50 °C
実験手順
Title compound 409 (0.403 g, 1.77 mmol) was dissolved in DMF (5.0 mL) and sodium hydride (60% in oil, 0.0.086 g, 2.13 mmol) was added. The reaction mixture was stirred at 50° C. for 30 minutes. Ethyl 7-bromoheptanoate (0.631 g, 2.66 mmol) was added and the reaction mixture was stirred at 50° C. for 16 hours. The mixture was cooled down to room temperature and quenched with water. The aqueous layer was extracted 3 times with at mixture of 75% ethyl acetate in hexanes. The combined organic extracts were washed with water and brine, dried over sodium sulfate, filtered and evaporated. The residue was purified by flash chromatography (30% ethyl acetate in hexanes) to afford title compound 410 (470 mg, 69%). MS (m/z): 384.4 (M+H).
後処理
- stirringthe reaction mixture was stirred at 50° C. for 16 hours
- temperatureThe mixture was cooled down to room temperature
- customquenched with water
- extractionThe aqueous layer was extracted 3 times
- additionwith at mixture of 75% ethyl acetate in hexanes
- washThe combined organic extracts were washed with water and brine
- dry with materialdried over sodium sulfate
- filtrationfiltered
- customevaporated
- customThe residue was purified by flash chromatography (30% ethyl acetate in hexanes)
出典と根拠
- ORDレコード
- ord-8a4c8c4e35544463ad4e8200b89db19a
- 出典データセット
- uspto-grants-2015_11
- 特許番号
- US09193749B2
関連ノート
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