Water → HCID 12018153, compound

HRID 1017585Notes

Reaction equation

HRID 1017585 reaction equation
[CH3:1][N:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[C:4]([C:11]2[C:12](=[O:32])[NH:13][C:14](=[O:31])[C:15]=2[C:16]2[CH:21]=[CH:20][CH:19]=[C:18]([S:22][CH2:23][C@H:24]3[CH2:28][O:27][C:26]([CH3:30])([CH3:29])[O:25]3)[CH:17]=2)=[CH:3]1.[OH:33]OS([O-])=O.[K+].[OH2:39]>CO>[CH3:1][N:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[C:4]([C:11]2[C:12](=[O:32])[NH:13][C:14](=[O:31])[C:15]=2[C:16]2[CH:21]=[CH:20][CH:19]=[C:18]([S:22]([CH2:23][C@H:24]3[CH2:28][O:27][C:26]([CH3:29])([CH3:30])[O:25]3)(=[O:33])=[O:39])[CH:17]=2)=[CH:3]1

Participants

5

Reactant 3

HCID 962Water2×HCID 12018149HCID 12018149, compoundHCID 23707502Potassium hydroxy sulfite

Product 1

HCID 12018153HCID 12018153, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of 3-(1-methylindol-3-yl)-4-[3-((R)-2,2-dimethyl-1,3-dioxolan-4-ylmethylsulfanyl)phenyl]-1H-pyrrole-2,5-dione (100 mg, 0.22 mmol) in methanol (20 mL) and water (5 mL) was added oxone in 5 mL of water at 0° C. The resulting suspension was stirred at 0° C. for 30 min., and was allowed to warm to rt and stirred for 5 h. The reaction mixture was then poured into ice water and extracted with dichloromethane. The organic layer was washed with NaS2O3 (15% aq.), NaCl (sat.) and dried over sodium sulfate. Preparative TLC with 2/4/4 of acetone/dichloromethane/hexane gave 40 mg of 3-(1-methylindol-3-yl)-4-[3-((R)-2,2-dimethyl-1,3-dioxolan-4-ylmethylsulfonyl)phenyl]-1H-pyrrole-2,5-dione. MS (ESI): (M+H)+ 481.

Workup

  1. temperatureto warm to rt
  2. stirringstirred for 5 h
  3. extractionextracted with dichloromethane
  4. washThe organic layer was washed with NaS2O3 (15% aq.), NaCl (sat.)
  5. dry with materialdried over sodium sulfate

Sources & evidence

ORD record
ord-e6b83ab0048047c582fd59a97b2982ff
Source dataset
uspto-grants-2002_11
Patent number
US06479490B2

Reaction notes

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