Potassium Permanganate → HCID 10295553, compound

HRID 397204Notes

Reaction equation

HRID 397204 reaction equation
[CH:1]1([S:6]([CH:8]([C:17]2[CH:22]=[CH:21][C:20]([Cl:23])=[C:19]([Cl:24])[CH:18]=2)[C:9]([NH:11][C:12]2[S:13][CH:14]=[CH:15][N:16]=2)=[O:10])=[O:7])[CH2:5][CH2:4][CH2:3][CH2:2]1.[Mn]([O-])(=O)(=O)=[O:26].[K+]>CO.O>[CH:1]1([S:6]([CH:8]([C:17]2[CH:22]=[CH:21][C:20]([Cl:23])=[C:19]([Cl:24])[CH:18]=2)[C:9]([NH:11][C:12]2[S:13][CH:14]=[CH:15][N:16]=2)=[O:10])(=[O:26])=[O:7])[CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

5

Reactant 2

HCID 516875Potassium PermanganateHCID 18172597HCID 18172597, compound

Product 1

HCID 10295553HCID 10295553, compoundYield 48%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Conditions

Temperature
25 °C

Procedure

A solution of rac-2-cyclopentanesulfinyl-2-(3,4-dichloro-phenyl)-N-thiazol-2-yl-acetamide (20 mg, 0.05 mmol) in methanol (2 mL) was stirred at 25° C. as a solution of potassium permanganate (9 mg, 0.06 mmol) in water (0.5 mL) was added. The mixture was stirred at 25° C. for 30 min and then was filtered. The filter cake was washed with dichloromethane and the combined filtrates were washed with sodium bicarbonate solution (10 mL) and brine (10 mL), then were dried over sodium sulfate, filtered and concentrated in vacuo. The product was purified by chromatography (Biotage Flash 12M column, 50/50 hexanes/ethyl acetate) to provide rac-2-cyclopentanesulfonyl-2-(3,4-dichloro-phenyl)-N-thiazol-2-yl-acetamide(10 mg, 48% yield) as a colorless oil: EI-HRMS m/e calculated for C16H16N2O3S2Cl2 (M+) 417.9979, found 417.9977.

Workup

  1. additionwas added
  2. filtrationwas filtered
  3. washThe filter cake was washed with dichloromethane
  4. washthe combined filtrates were washed with sodium bicarbonate solution (10 mL) and brine (10 mL)
  5. dry with materialwere dried over sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customThe product was purified by chromatography (Biotage Flash 12M column, 50/50 hexanes/ethyl acetate)

Sources & evidence

ORD record
ord-41237c20341c4987be4f4e155c748c9f
Source dataset
uspto-grants-2003_08
Patent number
US06608218B2

Reaction notes

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