反応式
F[C:2]1[CH:12]=[CH:11][C:5]([C:6]([O:8][CH2:9][CH3:10])=[O:7])=[CH:4][C:3]=1[C:13]1[C:14]2[CH:23]=[CH:22][N:21](S(C3C=CC(C)=CC=3)(=O)=O)[C:15]=2[C:16](=[O:20])[N:17]([CH3:19])[CH:18]=1.[C:34]1([OH:40])[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1.C(=O)([O-])[O-].[Cs+].[Cs+]>CS(C)=O>[CH3:19][N:17]1[CH:18]=[C:13]([C:3]2[CH:4]=[C:5]([CH:11]=[CH:12][C:2]=2[O:40][C:34]2[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=2)[C:6]([O:8][CH2:9][CH3:10])=[O:7])[C:14]2[CH:23]=[CH:22][NH:21][C:15]=2[C:16]1=[O:20]参加物
実験手順
A mixture of Example 9a (1.43 g, 3.05 mmol), phenol (0.0344 g, 3.66 mmol) and cesium carbonate (0.995, 3.05 mmol), in DMSO (15 mL) was heated at 110° C. for 12 hours. After cooling to room temperature, the reaction mixture was partitioned between water and ethyl acetate. The aqueous layer was extracted with additional ethyl acetate twice. The combined organic layers were washed with brine, dried over MgSO4, filtered, and concentrated. The residue was purified by flash chromatography (silica gel, 30-80% ethyl acetate/hexane) to afford 0.85 g (72%) of the title compound. 1H NMR (500 MHz, DMSO-d6) δ 1.31 (t, J=7.02 Hz, 3H), 3.55 (s, 3H), 4.32 (q, J=7.22 Hz, 2H), 6.23 (t, J=2.29 Hz, 1H), 6.97 (d, J=8.54 Hz, 1H), 7.06 (d, J=8.24 Hz, 2H), 7.17 (t, J=7.32 Hz, 1H), 7.28 (t, J=2.75 Hz, 1H), 7.36-7.51 (m, 3H), 7.94 (dd, J=8.7, 2.29 Hz, 1H), 8.04 (d, J=2.14 Hz, 1H), 12.02 (s, 1H). MS (ESI+) m/z 389.2 (M+H)+.
後処理
- customthe reaction mixture was partitioned between water and ethyl acetate
- extractionThe aqueous layer was extracted with additional ethyl acetate twice
- washThe combined organic layers were washed with brine
- dry with materialdried over MgSO4
- filtrationfiltered
- concentrationconcentrated
- customThe residue was purified by flash chromatography (silica gel, 30-80% ethyl acetate/hexane)
出典と根拠
- ORDレコード
- ord-b715ee3307b2443cab72685d8f09f67b
- 出典データセット
- uspto-grants-2016_03
- 特許番号
- US09296741B2
関連ノート
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