Ethanol → Fasiglifam

HRID 1848788ノート

反応式

HRID 1848788 の反応式
[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

参加物

4

反応物 2

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

生成物 1

HCID 24857286Fasiglifam収率 99.8%

試薬・触媒・溶媒 1

HCID 8471Triethylamine溶媒

反応条件

温度
50 °C

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-c50cb3cecb53416cb03b2fc816d45bda
出典データセット
uspto-grants-2015_02
特許番号
US08952185B2

反応ノート

読み込み中…