Trifluoroacetic acid → (6aR,7S,9aS,11S,13aS)-11-amino-5-benzyloxy-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 1417617Notes

Reaction equation

HRID 1417617 reaction equation
[NH2:1][C@@H:2]1[C:38]([CH3:40])([CH3:39])[C@H:37]2[C@@:5]3([O:33][C:9]4[C:10]5[CH2:11][N:12](C(OC(C)(C)C)=O)[C:13](=[O:25])[C:14]=5[CH:15]=[C:16]([O:17][CH2:18][C:19]5[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=5)[C:8]=4[CH2:7][C@:6]3([CH3:42])[C@@H:34]([CH3:41])[CH2:35][CH2:36]2)[CH2:4][CH2:3]1.C1(OC)C=CC=CC=1.FC(F)(F)C(O)=O.C(=O)([O-])O.[Na+]>ClCCl>[NH2:1][C@@H:2]1[C:38]([CH3:40])([CH3:39])[C@H:37]2[C@@:5]3([O:33][C:9]4[C:10]5[CH2:11][NH:12][C:13](=[O:25])[C:14]=5[CH:15]=[C:16]([O:17][CH2:18][C:19]5[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=5)[C:8]=4[CH2:7][C@:6]3([CH3:42])[C@@H:34]([CH3:41])[CH2:35][CH2:36]2)[CH2:4][CH2:3]1

Participants

6

Reactant 4

HCID 6422Trifluoroacetic acidHCID 7519AnisoleHCID 516892Sodium BicarbonateHCID 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 86753817(6aR,7S,9aS,11S,13aS)-11-amino-5-benzyloxy-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 73%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of Compound (45a) (50 mg, 0.087 mmol) in 5 ml of dry dichloromethane were added 30 μl (0.28 mmol) of anisole and 35 μl (0.45 mmol) of trifluoroacetic acid, and the mixture stirred for 3 hours at room temperature. Under ice-cooling, to the reaction mixture was added an aqueous saturated sodium hydrogen carbonate solution, followed by extraction with ethyl acetate. The extract was washed with water and an aqueous saturated sodium hydrogen carbonate solution, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure to give 30 mg (73%) of the crude Compound (46a) as a powdery material.

Workup

  1. temperatureUnder ice-cooling, to the reaction mixture
  2. extractionfollowed by extraction with ethyl acetate
  3. washThe extract was washed with water
  4. dry with materialan aqueous saturated sodium hydrogen carbonate solution, dried over anhydrous magnesium sulfate
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-b2f34ff962b04615a97094c1659273e9
Source dataset
uspto-grants-1999_03
Patent number
US05876984

Reaction notes

Loading…