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

HRID 1417633Notes

Reaction equation

HRID 1417633 reaction equation
C(OC([N:8]1[CH2:16][C:15]2[C:14]3[O:17][C@@:18]45[CH2:28][CH2:27][C@H:26]([OH:29])[C:25]([CH3:31])([CH3:30])[C@@H:24]4[CH2:23][CH2:22][C@H:21]([CH3:32])[C@@:19]5([CH3:33])[CH2:20][C:13]=3[C:12]([O:34][P:35]([O:44][C:45]3[CH:50]=[CH:49][CH:48]=[CH:47][CH:46]=3)([O:37][C:38]3[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=3)=[O:36])=[CH:11][C:10]=2[C:9]1=[O:51])=O)(C)(C)C.C1(OC)C=CC=CC=1.FC(F)(F)C(O)=O>ClCCl>[OH:29][C@@H:26]1[C:25]([CH3:31])([CH3:30])[C@H:24]2[C@@:18]3([O:17][C:14]4[C:15]5[CH2:16][NH:8][C:9](=[O:51])[C:10]=5[CH:11]=[C:12]([O:34][P:35]([O:44][C:45]5[CH:46]=[CH:47][CH:48]=[CH:49][CH:50]=5)([O:37][C:38]5[CH:39]=[CH:40][CH:41]=[CH:42][CH:43]=5)=[O:36])[C:13]=4[CH2:20][C@:19]3([CH3:33])[C@@H:21]([CH3:32])[CH2:22][CH2:23]2)[CH2:28][CH2:27]1

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 7519AnisoleHCID 86753840(6aR,7S,9aS,11S,13aS)-2-(t-butoxycarbonyl)-2,3,6,6a,7,8,9,9a, 10,11,12,13-dodecahydro-11-hydroxy-6a,7,10,10-tetramethyl-3-oxo-5-diphenoxyphosphinyloxy-1H-benzo[8,8a][1]benzopyrano[2,3-e]isoindole

Product 1

HCID 86753841(6aR,7S,9aS,11S,13aS)-2,3,6,6a,7,8,9,9a,10,11,12,13-dodecahydro-11-hydroxy-6a,7,10,10-tetramethyl-3-oxo-5-diphenoxyphosphinyloxy-1H-benzo[8,8a][1]benzopyrano[2,3-e]isoindoleYield 91.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of the above Compound (56a) (256 mg, 0.36 mmol) in 2.5 ml of dry dichloromethane were added 50 μl of anisole and 2.5 ml of trifluoroacetic acid, and the mixture stirred for 10 min at the same temperature, and then for one hour at room temperature. The reaction mixture was concentrated under reduced pressure. The residue was made basic with 7% aqueous sodium hydrogen carbonate solution, and extracted with ethyl acetate. The extract was washed with water, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was purified by a column chromatography (silica gel 15 g; ethyl acetate) to give 203 mg (91%) of Compound (57a).

Workup

  1. waitfor one hour at room temperature
  2. concentrationThe reaction mixture was concentrated under reduced pressure
  3. extractionextracted with ethyl acetate
  4. washThe extract was washed with water
  5. dry with materialdried over anhydrous magnesium sulfate
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was purified by a column chromatography (silica gel 15 g; ethyl acetate)

Sources & evidence

ORD record
ord-f645afbcbad640f4908ac8934868dc0f
Source dataset
uspto-grants-1999_03
Patent number
US05876984

Reaction notes

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