p-Toluenesulfonic acid → HCID 59389419, compound

HRID 2357902Notes

Reaction equation

HRID 2357902 reaction equation
[I:1][C:2]1[N:7]2[N:8]=[C:9]([S:11][CH3:12])[CH:10]=[C:6]2[C:5]([CH2:13][O:14]C2CCCCO2)=[CH:4][CH:3]=1.C1(C)C=CC(S(O)(=O)=O)=CC=1.C(=O)(O)[O-].[Na+]>CO>[CH:13]([C:5]1[C:6]2[N:7]([N:8]=[C:9]([S:11][CH3:12])[CH:10]=2)[C:2]([I:1])=[CH:3][CH:4]=1)=[O:14]

Participants

5

Reactant 3

HCID 6101p-Toluenesulfonic acidHCID 516892Sodium BicarbonateHCID 59389418HCID 59389418, compound

Product 1

HCID 59389419HCID 59389419, compoundYield 63.8%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

The compound of Example 101 (665 mg, 1.64 mmol) containing inseparable isomers was dissolved in methanol (15 mL). To this solution, p-toluenesulfonic acid (31.2 mg) was added and the mixture was stirred at room temperature for 2 hours. Subsequently, a saturated aqueous sodium bicarbonate solution was added and the mixture was extracted three times with ethyl acetate. The organic layer was washed with saturated brine and dried over sodium sulfate. The solvent was evaporated under reduced pressure and the resulting solid product was dissolved in dichloromethane (20 mL). To this solution, activated manganese dioxide (1.37 g) was added and the mixture was sonicated at room temperature for 3 hours. Subsequently, the mixture was filtered through Celite and the filtrate was evaporated. Purification of the resulting residue by silica gel column chromatography (hexane:ethyl acetate=20:1) afforded the title compound as a yellow powder (333 mg).

Workup

  1. extractionthe mixture was extracted three times with ethyl acetate
  2. washThe organic layer was washed with saturated brine
  3. dry with materialdried over sodium sulfate
  4. customThe solvent was evaporated under reduced pressure
  5. dissolutionthe resulting solid product was dissolved in dichloromethane (20 mL)
  6. additionwas added
  7. customthe mixture was sonicated at room temperature for 3 hours
  8. filtrationSubsequently, the mixture was filtered through Celite
  9. customthe filtrate was evaporated
  10. customPurification of the resulting residue by silica gel column chromatography (hexane:ethyl acetate=20:1)

Sources & evidence

ORD record
ord-7b9d95eeb995475ba15d066b7b192c1c
Source dataset
uspto-grants-2010_07
Patent number
US07763617B2

Reaction notes

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