Trifluoroacetic acid → (6aR,7S,9aS, 11R,12S,13aS)-5-benzyloxy-2,3,6,6a,7,8,9,9a,10,11,12,13-dodecahydro-11,12-dihydroxy-6a,7,10,10-tetramethyl-3-oxo-1H-benzo[8,8a][1]benzopyrano[2,3-e]isoindole

HRID 1417622ノート

反応式

HRID 1417622 の反応式
[CH2:1]([O:8][C:9]1[C:10]2[CH2:29][C@:28]3([CH3:43])[C@@H:30]([CH3:42])[CH2:31][CH2:32][C@H:33]4[C:34]([CH3:41])([CH3:40])[C@@H:35]([OH:39])[C@@H:36]([OH:38])[CH2:37][C@@:27]34[O:26][C:11]=2[C:12]2[CH2:13][N:14](C(OC(C)(C)C)=O)[C:15](=[O:18])[C:16]=2[CH:17]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C1(OC)C=CC=CC=1.FC(F)(F)C(O)=O.C(=O)([O-])O.[Na+]>ClCCl>[CH2:1]([O:8][C:9]1[C:10]2[CH2:29][C@:28]3([CH3:43])[C@@H:30]([CH3:42])[CH2:31][CH2:32][C@H:33]4[C:34]([CH3:41])([CH3:40])[C@@H:35]([OH:39])[C@@H:36]([OH:38])[CH2:37][C@@:27]34[O:26][C:11]=2[C:12]2[CH2:13][NH:14][C:15](=[O:18])[C:16]=2[CH:17]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

参加物

6

反応物 4

HCID 6422Trifluoroacetic acidHCID 7519AnisoleHCID 516892Sodium BicarbonateHCID 86753824(6aR,7S,9aS,11R,12S,13aS)-5-benzyloxy-2-(t-butoxycarbonyl)-2,3,6,6a,7,8,9,9a,10,11,12,13-dodecahydro-11,12-dihydroxy-6a,7,10,10-tetramethyl-3-oxo-1H-benzo[8,8a][1]benzopyrano[2,3-e]isoindole

生成物 1

HCID 86753825(6aR,7S,9aS, 11R,12S,13aS)-5-benzyloxy-2,3,6,6a,7,8,9,9a,10,11,12,13-dodecahydro-11,12-dihydroxy-6a,7,10,10-tetramethyl-3-oxo-1H-benzo[8,8a][1]benzopyrano[2,3-e]isoindole収率 96%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

To a solution of Compound (48a) (30 mg, 0.051 mmol) in 2.0 ml of dry dichloromethane were added 17 μl (0.156 mmol) of anisole and 40 μl (0.51 mmol) of trifluoroacetic acid under ice-cooling, and the mixture stirred for 1 hours at room temperature. Under ice-cooling, an aqueous saturated sodium hydrogen carbonate solution was added to the reaction mixture, which was followed by extraction with ethyl acetate. The extract was washed with water and saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was purified by a preparative thin layer chromatography (Merck, Kieselgel 60 F254, 0.5 mm; chloroform:methanol=10:1) to give 24 mg (96%) of Compound (49a).

後処理

  1. temperaturecooling
  2. temperatureUnder ice-cooling
  3. extractionwas followed by extraction with ethyl acetate
  4. washThe extract was washed with water and saturated brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was purified by a preparative thin layer chromatography (Merck, Kieselgel 60 F254, 0.5 mm; chloroform:methanol=10:1)

出典と根拠

ORDレコード
ord-7f8092fde62d46b584ad776d81ef7d7a
出典データセット
uspto-grants-1999_03
特許番号
US05876984

反応ノート

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