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 1417619Notes

Reaction equation

HRID 1417619 reaction equation
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]

Participants

5

Reactant 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

Product 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] isoindoleYield 82%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

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).

Workup

  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)

Sources & evidence

ORD record
ord-ca75ae97515546a080709d9786146bb9
Source dataset
uspto-grants-1999_03
Patent number
US05876984

Reaction notes

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