反応式
[F:1][C:2]1[CH:3]=[C:4]([C@H:10]2[NH:15][C@@H:14]([C@@H:16]([OH:18])[CH3:17])[CH2:13][O:12][CH2:11]2)[CH:5]=[C:6]([F:9])[C:7]=1[F:8].N1C=CC=CC=1.[C:25](Cl)(=[O:29])[C:26](Cl)=[O:27]>ClCCl.O>[CH3:17][C@H:16]1[C@H:14]2[CH2:13][O:12][CH2:11][C@@H:10]([C:4]3[CH:3]=[C:2]([F:1])[C:7]([F:8])=[C:6]([F:9])[CH:5]=3)[N:15]2[C:26](=[O:27])[C:25](=[O:29])[O:18]1参加物
実験手順
To a solution consisting of (S)-1-[(3R,5R)-5-(3,4,5-trifluorophenyl)morpholine-3-yl]ethanol (1.18 g) and pyridine (5 mL) in dichloromethane (20 mL) was dropwise added oxalyl chloride (1.18 mL) while cooling with ice. The resultant solution was stirred at the same temperature for 30 minutes, and then at room temperature for 1 hour. The reaction solution was diluted with water, and the organic layer was partitioned. The organic layer was then dried over anhydrous magnesium sulfate. Solvent was removed by distillation under reduced pressure, and the resulting residue was purified by silica gel column chromatography (heptane/ethyl acetate→ethyl acetate), to thereby obtain the titled compound (912 mg). The physical properties of the compound were as follows. ESI-MS; m/z 316 [M++H]. 1H-NMR (CDCl3) δ (ppm): 1.54 (d, J=7.2 Hz, 3H), 3.50 (dd, J=11.6, 11.6 Hz, 1H), 3.68 (dd, J=12.4, 8.0 Hz, 1H), 4.06 (dd, J=11.6, 4.4 Hz, 1H), 4.18 (dd, J=12.4, 4.8 Hz, 1H), 4.49 (ddd, J=12.0, 4.4, 4.0 Hz, 1H), 4.64-4.70 (m, 1H), 4.78 (dd, J=8.4, 5.2 Hz, 1H), 7.01 (dd, J=8.0, 6.4 Hz, 2H).
後処理
- temperaturewhile cooling with ice
- customthe organic layer was partitioned
- dry with materialThe organic layer was then dried over anhydrous magnesium sulfate
- customSolvent was removed by distillation under reduced pressure
- customthe resulting residue was purified by silica gel column chromatography (heptane/ethyl acetate→ethyl acetate)
出典と根拠
- ORDレコード
- ord-8bd413c2f5d44c51b68064144a54694e
- 出典データセット
- uspto-grants-2010_06
- 特許番号
- US07737141B2
関連ノート
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