Cesium carbonate → (S)-4-Benzyl-3-((S)-3-(isoxazol-3-yl)-3-(4-(2-(4-(trifluoromethyl)phenoxy)ethoxy)phenyl)propanoyl)oxazolidin-2-one

HRID 1675292노트

반응식

HRID 1675292 반응식
[CH2:1]([C@H:8]1[CH2:12][O:11][C:10](=[O:13])[N:9]1[C:14](=[O:32])[CH2:15][C@@H:16]([C:22]1[CH:27]=[CH:26][C:25]([O:28][CH2:29][CH2:30]Br)=[CH:24][CH:23]=1)[C:17]1[CH:21]=[CH:20][O:19][N:18]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(=O)([O-])[O-].[Cs+].[Cs+].[F:39][C:40]([F:49])([F:48])[C:41]1[CH:46]=[CH:45][C:44]([OH:47])=[CH:43][CH:42]=1>CN(C=O)C.O>[CH2:1]([C@H:8]1[CH2:12][O:11][C:10](=[O:13])[N:9]1[C:14](=[O:32])[CH2:15][C@H:16]([C:17]1[CH:21]=[CH:20][O:19][N:18]=1)[C:22]1[CH:27]=[CH:26][C:25]([O:28][CH2:29][CH2:30][O:47][C:44]2[CH:45]=[CH:46][C:41]([C:40]([F:39])([F:48])[F:49])=[CH:42][CH:43]=2)=[CH:24][CH:23]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

참가 물질

6

반응물 3

HCID 10796Cesium carbonateHCID 678744-(Trifluoromethyl)phenolHCID 59300638(S)-4-Benzyl-3-((S)-3-(4-(2-bromoethoxy)phenyl)-3-(isoxazol-3-yl)propanoyl)oxazolidin-2-one

생성물 1

HCID 59300648(S)-4-Benzyl-3-((S)-3-(isoxazol-3-yl)-3-(4-(2-(4-(trifluoromethyl)phenoxy)ethoxy)phenyl)propanoyl)oxazolidin-2-one수율 50%

시약·촉매·용매 2

HCID 962Water용매HCID 6228Dimethylformamide용매

실험 절차

The bromide 47.1 (100 mg, 0.2 mmol) was dissolved in DMF (2.0 mL). Cesium carbonate (260 mg, 0.8 mmol) and 4-trifluoromethylphenol (130 mg, 0.8 mmol) were added to the solution and the mixture was then heated with stirring for three hours. The reaction mixture was then cooled to room temperature and diluted with water. The mixture was extracted with EtOAc (2×50 mL). The combined organic layers were washed with 1M lithium chloride solution (1×25 mL), water (1×25 mL) and brine (1×25 mL) and dried over magnesium sulfate. The filtrate was concentrated under reduced pressure and the residue purified by medium pressure chromatography (silica, 0 to 60% EtOAc: hexanes) to obtain 47.2 (58 mg). MS ESI (pos.): m/e 581.2 (M+H).

후처리

  1. temperaturethe mixture was then heated
  2. extractionThe mixture was extracted with EtOAc (2×50 mL)
  3. washThe combined organic layers were washed with 1M lithium chloride solution (1×25 mL), water (1×25 mL) and brine (1×25 mL)
  4. dry with materialdried over magnesium sulfate
  5. concentrationThe filtrate was concentrated under reduced pressure
  6. customthe residue purified by medium pressure chromatography (silica, 0 to 60% EtOAc: hexanes)

출처 및 근거

ORD 기록
ord-78b68c8bf2954c7a82e5ff448f4dcb4a
출처 데이터셋
uspto-grants-2011_08
특허 번호
US08003648B2

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