Sodium Bicarbonate → (6aR,7S,9aS,13aS)-5-benzyloxy-2,3,6,6a,7,8,9,9a,10,11,12,13-dodecahydro-6a,7,10,10-tetramethyl-11-(1-oxa-4-azacyclohex-4-yl)imino-3-oxo-1H-benzo[8,8a][1]benzopyrano[2,3-e]isoindole

HRID 1417628Notes

Reaction equation

HRID 1417628 reaction equation
[CH2:1]([O:8][C:9]1[C:10]2[CH2:29][C@:28]3([CH3:48])[C@@H:30]([CH3:47])[CH2:31][CH2:32][C@H:33]4[C:34]([CH3:46])([CH3:45])[C:35](=[N:38][N:39]5[CH2:44][CH2:43][O:42][CH2:41][CH2:40]5)[CH2:36][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.Cl.O1CCOCC1.C(=O)([O-])O.[Na+]>>[CH2:1]([O:8][C:9]1[C:10]2[CH2:29][C@:28]3([CH3:48])[C@@H:30]([CH3:47])[CH2:31][CH2:32][C@H:33]4[C:34]([CH3:46])([CH3:45])[C:35](=[N:38][N:39]5[CH2:44][CH2:43][O:42][CH2:41][CH2:40]5)[CH2:36][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

Participants

4

Reactant 3

HCID 516892Sodium BicarbonateHCID 204431481,4-Dioxane hydrochlorideHCID 86753835(6aR,7S,9aS,13aS)-5-benzyloxy-2-(t-butoxycarbonyl)-2,3,6,6a,7,8,9,9a,10,11,12,13-dodecahydro-6a,7,10,10-tetramethyl-11-(1-oxa-4-azacyclohex-4-yl)imino-3-oxo-1H-benzo[8,8a][1]benzopyrano[2,3-e]isoindole

Product 1

HCID 86753836(6aR,7S,9aS,13aS)-5-benzyloxy-2,3,6,6a,7,8,9,9a,10,11,12,13-dodecahydro-6a,7,10,10-tetramethyl-11-(1-oxa-4-azacyclohex-4-yl)imino-3-oxo-1H-benzo[8,8a][1]benzopyrano[2,3-e]isoindoleYield 100.4%

Procedure

To the above Compound (60) (265 mg, 0.40 mmol) was added 2.0 ml of 4N HCl/dioxane solution, and the mixture stirred for one hour at room temperature. The reaction mixture was made basic with 7% aqueous sodium hydrogen carbonate solution, and extracted with ethyl acetate. The extract was concentrated under reduced pressure. The residue was purified by a silica gel column chromatography (silica gel 10 g; ethyl acetate:methanol=97:3) to give 224 mg (100%) of Compound (61).

Workup

  1. extractionextracted with ethyl acetate
  2. concentrationThe extract was concentrated under reduced pressure
  3. customThe residue was purified by a silica gel column chromatography (silica gel 10 g; ethyl acetate:methanol=97:3)

Sources & evidence

ORD record
ord-7f032c1c6331410d9137276a33dd666f
Source dataset
uspto-grants-1999_03
Patent number
US05876984

Reaction notes

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