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[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]1참가 물질
실험 절차
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).
후처리
- 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)
출처 및 근거
- ORD 기록
- ord-8bd413c2f5d44c51b68064144a54694e
- 출처 데이터셋
- uspto-grants-2010_06
- 특허 번호
- US07737141B2
연결된 노트
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