Water → HCID 22504420, compound

HRID 1814083Notes

Reaction equation

HRID 1814083 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-f77e33e7b3bd4d8eaa678cb06e0b6607
Source dataset
uspto-grants-2005_04
Patent number
US06875770B2

Reaction notes

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