Water → (S)-methyl 2-(6-((4'-(cyclopentyloxy)-2',6'-dimethylbiphenyl-3-yl)methoxy)-2,3-dihydrobenzofuran-3-yl)acetate

HRID 2280650노트

반응식

HRID 2280650 반응식
CS([O:5][CH:6]1[CH2:10][CH2:9][CH2:8][CH2:7]1)(=O)=O.O[C:12]1[CH:17]=[C:16]([CH3:18])[C:15]([C:19]2[CH:24]=[CH:23][CH:22]=[C:21]([CH2:25][O:26][C:27]3[CH:40]=[CH:39][C:30]4[C@H:31]([CH2:34][C:35]([O:37][CH3:38])=[O:36])[CH2:32][O:33][C:29]=4[CH:28]=3)[CH:20]=2)=[C:14]([CH3:41])[CH:13]=1.C(=O)([O-])[O-].[Cs+].[Cs+].O>CN(C)C=O>[CH:6]1([O:5][C:12]2[CH:13]=[C:14]([CH3:41])[C:15]([C:19]3[CH:24]=[CH:23][CH:22]=[C:21]([CH2:25][O:26][C:27]4[CH:40]=[CH:39][C:30]5[C@H:31]([CH2:34][C:35]([O:37][CH3:38])=[O:36])[CH2:32][O:33][C:29]=5[CH:28]=4)[CH:20]=3)=[C:16]([CH3:18])[CH:17]=2)[CH2:10][CH2:9][CH2:8][CH2:7]1

참가 물질

6

반응물 4

HCID 962WaterHCID 10796Cesium carbonateHCID 13066113Cyclopentyl methanesulfonateHCID 57414918(S)-methyl 2-(6-((4'-hydroxy-2',6'-dimethylbiphenyl-3-yl)methoxy)-2,3-dihydrobenzofuran-3-yl)acetate

생성물 1

HCID 73388924(S)-methyl 2-(6-((4'-(cyclopentyloxy)-2',6'-dimethylbiphenyl-3-yl)methoxy)-2,3-dihydrobenzofuran-3-yl)acetate수율 30%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

반응 조건

온도
80 °C

실험 절차

Cyclopentyl methanesulfonate 10c (50 mg, 0.28 mmol), (S)-methyl 2-(6-((4′-hydroxy-2′,6′-dimethylbiphenyl-3-yl)methoxy)-2,3-dihydrobenzofuran-3-yl)acetate 3 h (60 mg, 0.14 mmol), and cesium carbonate (100 mg, 0.30 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 mixture was mixed with 10 mL of water and extracted with ethyl acetate (20 mL×2). 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 the reduced pressure and the residue was purified by elution system B to obtain the title compound (S)-methyl 2-(6-((4′-(cyclopentyloxy)-2′,6′-dimethylbiphenyl-3-yl)methoxy)-2,3-dihydrobenzofuran-3-yl)acetate 10d (40 mg, yield 30.0%) as a colorless slime.

후처리

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

출처 및 근거

ORD 기록
ord-689dee51956d4620b4e5fea72547cfd4
출처 데이터셋
uspto-grants-2015_09
특허 번호
US09139548B2

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