Ethyl Acetate → methyl (S)-2-(6-((4'-((1-(tert-butoxycarbonyl)piperidin-4-yl)oxy)-2',6'-dimethylbiphenyl-3-yl)methoxy)-2,3-dihydrobenzofuran-3-yl)acetate

HRID 2280638노트

반응식

HRID 2280638 반응식
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([O:14]S(C)(=O)=O)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].O[C:20]1[CH:25]=[C:24]([CH3:26])[C:23]([C:27]2[CH:32]=[CH:31][CH:30]=[C:29]([CH2:33][O:34][C:35]3[CH:48]=[CH:47][C:38]4[C@H:39]([CH2:42][C:43]([O:45][CH3:46])=[O:44])[CH2:40][O:41][C:37]=4[CH:36]=3)[CH:28]=2)=[C:22]([CH3:49])[CH:21]=1.C(=O)([O-])[O-].[Cs+].[Cs+].C(OCC)(=O)C>CN(C)C=O>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([O:14][C:20]2[CH:21]=[C:22]([CH3:49])[C:23]([C:27]3[CH:32]=[CH:31][CH:30]=[C:29]([CH2:33][O:34][C:35]4[CH:48]=[CH:47][C:38]5[C@H:39]([CH2:42][C:43]([O:45][CH3:46])=[O:44])[CH2:40][O:41][C:37]=5[CH:36]=4)[CH:28]=3)=[C:24]([CH3:26])[CH:25]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

참가 물질

6

반응물 4

HCID 8857Ethyl AcetateHCID 10796Cesium carbonateHCID 41848691-(tert-Butoxycarbonyl)-4-(methanesulfonyloxy)piperidineHCID 57414918(S)-methyl 2-(6-((4'-hydroxy-2',6'-dimethylbiphenyl-3-yl)methoxy)-2,3-dihydrobenzofuran-3-yl)acetate

생성물 1

HCID 89701758methyl (S)-2-(6-((4'-((1-(tert-butoxycarbonyl)piperidin-4-yl)oxy)-2',6'-dimethylbiphenyl-3-yl)methoxy)-2,3-dihydrobenzofuran-3-yl)acetate수율 35%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

반응 조건

온도
80 °C

실험 절차

4-[(Methylsulfonyl)oxy]piperidine-1-carboxylic acid tert-butyl ester (134 mg, 0.48 mmol), (S)-methyl 2-(6-((4′-hydroxy-2′,6′-dimethylbiphenyl-3-yl)methoxy)-2,3-dihydrobenzofuran-3-yl)acetate 3 h (200 mg, 0.48 mmol) and cesium carbonate (470 mg, 1.43 mmol) were dissolved in 10 mL of N,N-dimethylformamide. The reaction mixture was heated to 80° C. and stirred for 12 hours. The resulting solution was mixed with 30 mL of ethyl acetate. The organic phase was washed with water (20 mL×2) and saturated sodium chloride solution (20 mL) successively, dried with anhydrous sodium sulfate and filtered. The filtrate was concentrated under reduced pressure and the residue was purified by elution system B to obtain the title compound methyl (S)-2-(6-((4′-((1-(tert-butoxycarbonyl)piperidin-4-yl)oxy)-2′,6′-dimethylbiphenyl-3-yl)methoxy)-2,3-dihydrobenzofuran-3-yl)acetate 3j (101 mg, yield 35.0%) as a colorless slime.

후처리

  1. washThe organic phase was washed with water (20 mL×2) and saturated sodium chloride solution (20 mL) successively
  2. dry with materialdried with anhydrous sodium sulfate
  3. filtrationfiltered
  4. concentrationThe filtrate was concentrated under reduced pressure
  5. customthe residue was purified by elution system B

출처 및 근거

ORD 기록
ord-489f1775a61d48e7815f08d888843f05
출처 데이터셋
uspto-grants-2015_09
특허 번호
US09139548B2

반응 노트

불러오는 중…