반응식
[F:1][C:2]([F:28])([F:27])[O:3][C:4]1[CH:5]=[C:6]([C:10]2[C:14]3[CH:15]=[C:16]([C:19]4[O:23][C:22]([C@@H:24]([OH:26])[CH3:25])=[N:21][N:20]=4)[CH:17]=[CH:18][C:13]=3[O:12][CH:11]=2)[CH:7]=[CH:8][CH:9]=1.[C:29](O)(=[O:31])[CH3:30].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OCC)=O)=NC(OCC)=O.C1(C)C=CC=CC=1>O1CCCC1.C(OCC)(=O)C>[C:29]([O:26][C@@H:24]([C:22]1[O:23][C:19]([C:16]2[CH:17]=[CH:18][C:13]3[O:12][CH:11]=[C:10]([C:6]4[CH:7]=[CH:8][CH:9]=[C:4]([O:3][C:2]([F:27])([F:1])[F:28])[CH:5]=4)[C:14]=3[CH:15]=2)=[N:20][N:21]=1)[CH3:25])(=[O:31])[CH3:30]참가 물질
반응물 4
생성물 1
시약·촉매·용매 2
실험 절차
To a solution of (1S)-1-[5-[3-[3-(trifluoromethoxy)phenyl]-1-benzofuran-5-yl]-1,3,4-oxadiazol-2-yl]ethanol (390 mg, 1.00 mmol), acetic acid (0.114 mL, 2.00 mmol) and triphenylphosphine (394 mg, 1.50 mmol) in tetrahydrofuran (5 mL) was added dropwise 40% diethyl azodicarboxylate-toluene solution (0.653 mL, 1.50 mmol) at 0° C., and the resulting mixture was stirred overnight at room temperature. The reaction mixture was diluted with ethyl acetate, washed with saturated aqueous sodium hydrogen carbonate solution and saturated brine, dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The residue was purified by basic silica gel column chromatography (hexane/ethyl acetate=10/1-0/1) to give the title compound (406 mg, yield 94%) as a colorless oil.
후처리
- washwashed with saturated aqueous sodium hydrogen carbonate solution and saturated brine
- dry with materialdried over anhydrous magnesium sulfate
- concentrationconcentrated under reduced pressure
- customThe residue was purified by basic silica gel column chromatography (hexane/ethyl acetate=10/1-0/1)
출처 및 근거
- ORD 기록
- ord-bf932d1d22194f16afe04bd7cdfc4a71
- 출처 데이터셋
- uspto-grants-2013_07
- 특허 번호
- US08492378B2
연결된 노트
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