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Azobisisobutyronitrile → 2-[(1S)-2-{[4-fluoro-5-(hydroxymethyl)isoxazol-3-yl]oxy}-1-methylethyl]-1H-isoindole-1,3(2H)-dione

HRID 1026265
ノート
印刷プレビュー

反応式

HRID 1026265 の反応式
[F:1][C:2]1[C:3]([O:8][CH2:9][C@@H:10]([N:12]2[C:20](=[O:21])[C:19]3[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=3)[C:13]2=[O:22])[CH3:11])=[N:4][O:5][C:6]=1[CH3:7].BrN1C(=[O:29])CCC1=O.N(C(C)(C)C#N)=NC(C)(C)C#N.FC(C1C=CC=CC=1)(F)F>O>[F:1][C:2]1[C:3]([O:8][CH2:9][C@@H:10]([N:12]2[C:20](=[O:21])[C:19]3[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=3)[C:13]2=[O:22])[CH3:11])=[N:4][O:5][C:6]=1[CH2:7][OH:29]
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

6

反応物 4

HCID 6547AzobisisobutyronitrileHCID 7368(Trifluoromethyl)benzeneHCID 67184N-bromobutanimideHCID 67778378HCID 67778378、化合物

生成物 1

HCID 677778302-[(1S)-2-{[4-fluoro-5-(hydroxymethyl)isoxazol-3-yl]oxy}-1-methylethyl]-1H-isoindole-1,3(2H)-dione収率 29.3%

試薬・触媒・溶媒 1

HCID 962
Water
溶媒

反応条件

温度
100 °C

実験手順

A mixture of 2-{(1S)-2-[(4-fluoro-5-methylisoxazol-3-yl)oxy]-1-methylethyl}-1H-isoindole-1,3(2H)-dione (383 mg), N-bromosuccinimide (269 mg), 2,2′-azobis(2-methylpropionitrile) (20.7 mg) and (trifluoromethyl)benzene (5 mL) was stirred at 100° C. overnight. Water was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The obtained organic layer was washed with saturated brine, and dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (hexane/ethyl acetate). The obtained residue was mixed with 1-methylpyrrolidin-2-one (5 mL) and water (10 mL), and the mixture was stirred at 105° C. overnight. The reaction mixture was extracted with ethyl acetate, and the obtained organic layer was washed with saturated brine, and dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (hexane/ethyl acetate) to give the title compound as a colorless oil (118 mg).

後処理

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe obtained organic layer was washed with saturated brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customthe solvent was evaporated under reduced pressure
  5. customThe residue was purified by silica gel column chromatography (hexane/ethyl acetate)
  6. additionThe obtained residue was mixed with 1-methylpyrrolidin-2-one (5 mL) and water (10 mL)
  7. stirringthe mixture was stirred at 105° C. overnight
  8. extractionThe reaction mixture was extracted with ethyl acetate
  9. washthe obtained organic layer was washed with saturated brine
  10. dry with materialdried over anhydrous magnesium sulfate
  11. customthe solvent was evaporated under reduced pressure
  12. customThe residue was purified by silica gel column chromatography (hexane/ethyl acetate)

出典と根拠

ORDレコード
ord-5c7a8aabfef64c41aa30fdf82571fa4f
出典データセット
uspto-grants-2014_05
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08729102B2

反応ノート

読み込み中…

このページの内容参加物反応条件実験手順後処理出典と根拠反応ノート