Water → HCID 22504420, compound

HRID 1838345Notes

Reaction equation

HRID 1838345 reaction equation
[O:1]1[CH2:6][CH2:5][C:4]([C:7]2[N:8]([S:18]([C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=3)(=[O:20])=[O:19])[C:9]3[C:14]([CH:15]=2)=[CH:13][C:12]([S:16][CH3:17])=[CH:11][CH:10]=3)=[CH:3][CH2:2]1.OOS([O-])=O.[K+].[OH2:33].O1CCCC1.[OH2:39]>>[O:1]1[CH2:6][CH2:5][C:4]([C:7]2[N:8]([S:18]([C:21]3[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=3)(=[O:20])=[O:19])[C:9]3[C:14]([CH:15]=2)=[CH:13][C:12]([S:16]([CH3:17])(=[O:39])=[O:33])=[CH:11][CH:10]=3)=[CH:3][CH2:2]1

Participants

5

Reactant 4

HCID 962WaterHCID 21881883Oxolane--water (1/1)HCID 225044022-(5,6-dihydro-2H-4-pyranyl)-1-benzenesulfonyl-5-methylthioindoleHCID 23707502Potassium hydroxy sulfite

Product 1

HCID 22504420HCID 22504420, compound

Procedure

To a solution of the compound obtained in Example 14 (2) (33.7 mg) in a mixture of tetrahydrofuran/water (3:1, 4 ml), OXONE (registered trademark) (134 mg) was added at 15 to 30° C. and the mixture was stirred for 15 hours. The reaction solution was then poured into water, extracted with dichloromethane, dried over anhydrous magnesium sulfate, filtered and concentrated under reduced pressure. The resulting residue was separated using silica gel preparative thin-layer chromatography (hexane:ethyl acetate=1:1) to obtain 28.8 mg of the desired product as a white powder.

Workup

  1. additionwas added at 15 to 30° C.
  2. extractionextracted with dichloromethane
  3. dry with materialdried over anhydrous magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customThe resulting residue was separated

Sources & evidence

ORD record
ord-2ce51887f9a04421a8f4086e5afc9466
Source dataset
uspto-grants-2004_01
Patent number
US06673797B1

Reaction notes

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