Acetyl chloride → (6aR,7S,9aS,11S,13aS)-11-acetylamino-5-benzyloxy-2-(t-butoxycarbonyl)-2,3,6,6a,7,8,9,9a,10,11,12,13-dodecahydro-6a,7,10,10-tetramethyl-3-oxo-1H-benzo[8,8a][1]benzopyrano [2,3-e] isoindole

HRID 1417619노트

반응식

HRID 1417619 반응식
C(N(CC)CC)C.[C:8](Cl)(=[O:10])[CH3:9].[NH2:12][C@@H:13]1[C:49]([CH3:51])([CH3:50])[C@H:48]2[C@@:16]3([O:44][C:20]4[C:21]5[CH2:22][N:23]([C:37]([O:39][C:40]([CH3:43])([CH3:42])[CH3:41])=[O:38])[C:24](=[O:36])[C:25]=5[CH:26]=[C:27]([O:28][CH2:29][C:30]5[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=5)[C:19]=4[CH2:18][C@:17]3([CH3:53])[C@@H:45]([CH3:52])[CH2:46][CH2:47]2)[CH2:15][CH2:14]1>ClCCl>[C:8]([NH:12][C@@H:13]1[C:49]([CH3:51])([CH3:50])[C@H:48]2[C@@:16]3([O:44][C:20]4[C:21]5[CH2:22][N:23]([C:37]([O:39][C:40]([CH3:43])([CH3:42])[CH3:41])=[O:38])[C:24](=[O:36])[C:25]=5[CH:26]=[C:27]([O:28][CH2:29][C:30]5[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=5)[C:19]=4[CH2:18][C@:17]3([CH3:53])[C@@H:45]([CH3:52])[CH2:46][CH2:47]2)[CH2:15][CH2:14]1)(=[O:10])[CH3:9]

참가 물질

5

반응물 3

HCID 6367Acetyl chlorideHCID 8471TriethylamineHCID 86753816(6aR,7S,9aS,11S,13aS)-11-amino-5-benzyloxy-2-(t-butoxycarbonyl)-2,3,6,6a,7,8,9,9a,10,11,12,13-dodecahydro-6a,7,10,10-tetramethyl-3-oxo-1H-benzo[8,8a][1]benzopyrano[2,3-e]isoindole

생성물 1

HCID 86753819(6aR,7S,9aS,11S,13aS)-11-acetylamino-5-benzyloxy-2-(t-butoxycarbonyl)-2,3,6,6a,7,8,9,9a,10,11,12,13-dodecahydro-6a,7,10,10-tetramethyl-3-oxo-1H-benzo[8,8a][1]benzopyrano [2,3-e] isoindole수율 82%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

Under nitrogen, 25 μl (0.18 mmol) of triethylamine and 8 μl (0.11 mmol) of acetyl chloride was added to a solution of Compound (45a) (50 mg, 0.087 mmol) in 2.0 ml of dry dichloromethane under ice-cooling, and the mixture stirred for 40 min at the same temperature. After addition of ice-water, the reaction was extracted with ethyl acetate. The extract was washed with aqueous saturated sodium hydrogen carbonate and water, 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=30:1) to give 44 mg (82%) of Compound (45b).

후처리

  1. temperaturecooling
  2. extractionthe reaction was extracted with ethyl acetate
  3. washThe extract was washed with aqueous saturated sodium hydrogen carbonate and water
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by a preparative thin layer chromatography (Merck, Kieselgel 60 F254, 0.5 mm; chloroform:methanol=30:1)

출처 및 근거

ORD 기록
ord-ca75ae97515546a080709d9786146bb9
출처 데이터셋
uspto-grants-1999_03
특허 번호
US05876984

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