Methanol → HCID 178499140, compound

HRID 1507624Notes

Reaction equation

HRID 1507624 reaction equation
[CH3:1][O:2][C:3]([C:5]1[N:6]=[C:7](SC)[NH:8][C:9]=1[C:10]1[CH:15]=[CH:14][C:13]([F:16])=[CH:12][CH:11]=1)=[O:4].O[O:20][S:21]([O-:23])=O.[K+].[CH3:25]O>O>[CH3:1][O:2][C:3]([C:5]1[N:6]=[C:7]([S:21]([CH3:25])(=[O:23])=[O:20])[NH:8][C:9]=1[C:10]1[CH:15]=[CH:14][C:13]([F:16])=[CH:12][CH:11]=1)=[O:4]

Participants

5

Reactant 3

HCID 887MethanolHCID 23707502Potassium hydroxy sulfiteHCID 178499139HCID 178499139, compound

Product 1

HCID 178499140HCID 178499140, compoundYield 92%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a stirred solution of compound 8 (19.3 g, 72.5 mmol) in MeOH (500 mL) was added a solution of OXONE (133 g) in water (500 mL) dropwise at rt in 1 h. The resulting mixture was stirred at rt for 4 h and then concentrated under reduced pressure. The slurry aqueous mixture was extracted with DCM (200 mL×4). The combined extracts were washed with brine (100 mL×2), dried over anhydrous MgSO4, filtered, and evaporated to afford sulfone 10 (19.8 g, 92%) as a white solid. ESI MS m/z 299.2 (M+H)+.

Workup

  1. concentrationconcentrated under reduced pressure
  2. extractionThe slurry aqueous mixture was extracted with DCM (200 mL×4)
  3. washThe combined extracts were washed with brine (100 mL×2)
  4. dry with materialdried over anhydrous MgSO4
  5. filtrationfiltered
  6. customevaporated

Sources & evidence

ORD record
ord-81f2df2387714f609464f0e18b95c502
Source dataset
uspto-grants-2015_12
Patent number
US09221805B2

Reaction notes

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