Water → 1-Benzenesulfonyl-2-(2-ethoxycarbonylfuran-5-yl-methyl)-5-methanesulfonylindole

HRID 1838384Notes

Reaction equation

[C:1]1([S:7]([N:10]2[C:18]3[C:13](=[CH:14][C:15](SC)=[CH:16][CH:17]=3)[CH:12]=[C:11]2[CH2:21][C:22]2[O:26][C:25]([C:27]([O:29][CH2:30][CH3:31])=[O:28])=[CH:24][CH:23]=2)(=O)=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.O[O:33][S:34]([O-:36])=O.[K+].[C:38](=O)([O-])O.[Na+].[OH2:43]>O1CCCC1>[C:1]1([S:7]([N:10]2[C:18]3[C:13](=[CH:14][C:15]([S:34]([CH3:38])(=[O:36])=[O:33])=[CH:16][CH:17]=3)[CH:12]=[C:11]2[CH2:21][C:22]2[O:26][C:25]([C:27]([O:29][CH2:30][CH3:31])=[O:28])=[CH:24][CH:23]=2)(=[O:8])=[O:43])[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

Conditions

Temperature: 22.5 °C

Procedure

To a solution of the compound obtained in Example 30 (3) (0.183 g) in a mixture of tetrahydrofuran (2 ml) and water (2 ml), OXONE (registered trademark) (0.4939 g) was added under ice-cooling and the mixture was stirred for 30 minutes and at 15 to 30° C. for 1.5 hours. A saturated aqueous sodium hydrogencarbonate solution was added thereto, and the mixture was extracted with ethyl acetate, dried over anhydrous magnesium sulfate, filtered and concentrated under reduced pressure. The resulting residue was separated using silica gel column chromatography (hexane:ethyl acetate=1:1) to obtain 0.1722 g of the desired product.

Workup

additionwas added under ice-
temperaturecooling
extractionthe mixture was extracted with ethyl acetate
dry with materialdried over anhydrous magnesium sulfate
filtrationfiltered
concentrationconcentrated under reduced pressure
customThe resulting residue was separated

Sources & evidence

ORD record: ord-bab89a9b5f0649f2866dc7f331e6a5b0
Source dataset: uspto-grants-2004_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06673797B1

Reaction notes

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