Potassium hydroxy sulfite → HCID 57663196, compound

HRID 548702Notes

Reaction equation

HRID 548702 reaction equation
S1[C:5]2[CH:6]=[CH:7][C:8]([O:10][C:11]3[CH:12]=[C:13]([CH:23]=[C:24]([O:26][C@@H:27]([CH3:31])[CH2:28][O:29][CH3:30])[CH:25]=3)[C:14]([NH:16][C:17]3[CH:21]=[CH:20][N:19]([CH3:22])[N:18]=3)=[O:15])=[CH:9][C:4]=2[CH:3]=[CH:2]1.O[O:33][S:34]([O-:36])=O.[K+]>CO.O>[O:33]=[S:34]1(=[O:36])[C:5]2[CH:6]=[CH:7][C:8]([O:10][C:11]3[CH:12]=[C:13]([CH:23]=[C:24]([O:26][C@@H:27]([CH3:31])[CH2:28][O:29][CH3:30])[CH:25]=3)[C:14]([NH:16][C:17]3[CH:21]=[CH:20][N:19]([CH3:22])[N:18]=3)=[O:15])=[CH:9][C:4]=2[CH:3]=[CH:2]1

Participants

5

Reactant 2

HCID 23707502Potassium hydroxy sulfiteHCID 57663177HCID 57663177, compound

Product 1

HCID 57663196HCID 57663196, compoundYield 58.7%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent2×

Procedure

To a solution of 3-(1-benzothien-5-yloxy)-5-{[(1S)-1-methyl-2-(methyloxy)ethyl]oxy}-N-(1-methyl-1H-pyrazol-3-yl)benzamide (178 mg, 0.41 mmol) in methanol (3 mL) at 0° C. was added dropwise a solution of oxone (752 mg, 1.22 mmol) in water (3 mL). The resultant cloudy slurry was allowed to warm to RT and stir for 16 hours. Water (20 mL) was added and the mixture extracted with DCM (3×20 mL). The combined extracts were dried (MgSO4), filtered and evaporated. The material was chromatographed on silica, eluting with 0-3% methanol in DCM, to give the desired compound as yellow oil (113 mg). m/z 470 (M+H)+

Workup

  1. extractionthe mixture extracted with DCM (3×20 mL)
  2. dry with materialThe combined extracts were dried (MgSO4)
  3. filtrationfiltered
  4. customevaporated
  5. customThe material was chromatographed on silica
  6. washeluting with 0-3% methanol in DCM

Sources & evidence

ORD record
ord-6c4f57e061784155bb03fe5945775542
Source dataset
uspto-grants-2011_05
Patent number
US07943607B2

Reaction notes

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