Ethanol → Fasiglifam

HRID 1848788노트

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HRID 1848788 반응식
[CH3:1][C:2]1[CH:7]=[C:6]([O:8][CH2:9][CH2:10][CH2:11][S:12]([CH3:15])(=[O:14])=[O:13])[CH:5]=[C:4]([CH3:16])[C:3]=1[C:17]1[CH:22]=[CH:21][CH:20]=[C:19]([CH2:23][O:24][C:25]2[CH:37]=[CH:36][C:28]3[C:29]([CH2:32][C:33]([OH:35])=[O:34])=[CH:30][O:31][C:27]=3[CH:26]=2)[CH:18]=1.C(O)C>C(N(CC)CC)C>[CH3:16][C:4]1[CH:5]=[C:6]([O:8][CH2:9][CH2:10][CH2:11][S:12]([CH3:15])(=[O:14])=[O:13])[CH:7]=[C:2]([CH3:1])[C:3]=1[C:17]1[CH:22]=[CH:21][CH:20]=[C:19]([CH2:23][O:24][C:25]2[CH:37]=[CH:36][C:28]3[C@H:29]([CH2:32][C:33]([OH:35])=[O:34])[CH2:30][O:31][C:27]=3[CH:26]=2)[CH:18]=1

참가 물질

4

반응물 2

HCID 702EthanolHCID 86706791[6-({2',6'-Dimethyl-4'-[3-(methylsulfonyl)propoxy]biphenyl-3-yl}methoxy)-1-benzofuran-3-yl]acetic acid

생성물 1

HCID 24857286Fasiglifam수율 99.8%

시약·촉매·용매 1

HCID 8471Triethylamine용매

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온도
50 °C

실험 절차

Under an argon atmosphere, to [6-({2′,6′-dimethyl-4′-[3-(methylsulfonyl)propoxy]biphenyl-3-yl}methoxy)-1-benzofuran-3-yl]acetic acid (522 mg), dichloro[(+)-1,2-bis((2R,5R)-2,5-diisopropylphosphorano)benzene]ruthenium (II)-N,N-dimethylformamide complex (7.4 mg) in an autoclave container was added a solution of dehydrated ethanol (6 mL) containing triethylamine (0.139 mL), and the mixture was stirred at 50° C. for 24 hr under a hydrogen atmosphere (1 MPa). The reaction mixture was concentrated, 10% aqueous citric acid solution (25 mL) and ethyl acetate (25 mL) were added, and an extraction operation was performed. The aqueous layer was extracted with ethyl acetate (25 mL), and the combined organic layer was washed with water (25 mL), dried over sodium sulfate and concentrated. The crude product was washed with diisopropyl ether. After filtration, the obtained solid was dried at 50° C. under reduced pressure to give the title compound (523 mg) as white crystals. 80.0% ee.

후처리

  1. concentrationThe reaction mixture was concentrated
  2. addition10% aqueous citric acid solution (25 mL) and ethyl acetate (25 mL) were added
  3. extractionThe aqueous layer was extracted with ethyl acetate (25 mL)
  4. washthe combined organic layer was washed with water (25 mL)
  5. dry with materialdried over sodium sulfate
  6. concentrationconcentrated
  7. washThe crude product was washed with diisopropyl ether
  8. filtrationAfter filtration
  9. customthe obtained solid was dried at 50° C. under reduced pressure

출처 및 근거

ORD 기록
ord-c50cb3cecb53416cb03b2fc816d45bda
출처 데이터셋
uspto-grants-2015_02
특허 번호
US08952185B2

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