p-Toluenesulfonic acid → HCID 22734057, compound

HRID 2084771Notes

Reaction equation

HRID 2084771 reaction equation
[C:1]1(C)C=CC(S(O)(=O)=O)=CC=1.Cl[C:13]1[CH:14]=[N:15][CH:16]=[C:17](Cl)[C:18]=1[CH2:19][CH:20]([C:22]1[C:27]2[CH2:28][C:29](C)(C)[O:30][C:26]=2[C:25]([O:33][CH3:34])=[CH:24][CH:23]=1)O>CO>[CH3:34][O:33][C:25]1[C:26]2[O:30][CH2:29][CH:28]([CH3:1])[C:27]=2[C:22]([CH2:20][CH2:19][C:18]2[CH:13]=[CH:14][N:15]=[CH:16][CH:17]=2)=[CH:23][CH:24]=1

Participants

4

Reactant 2

HCID 6101p-Toluenesulfonic acidHCID 22734123HCID 22734123, compound

Product 1

HCID 22734057HCID 22734057, compoundYield 68.4%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

p-Toluenesulfonic acid (1.0 g) was added to a solution (50 ml) of Compound 45a (2.0 g) obtained in Step A of Example 45 in methanol at room temperature, followed by heating under reflux. The reaction solution was cooled and then the solvent was distilled off under reduced pressure. A saturated aqueous solution of sodium bicarbonate was added to the residue, followed by extraction with chloroform. The organic layer was washed with a saturated saline and dried over anhydrous magnesium sulfate, and the solvent was distilled off under reduced pressure. The residue was purified by silica gel column chromatography (chloroform) to give Compound 57 (1.0 g, 48.2%) as a pale-yellow oily substance.

Workup

  1. temperatureby heating
  2. temperatureunder reflux
  3. temperatureThe reaction solution was cooled
  4. distillationthe solvent was distilled off under reduced pressure
  5. additionA saturated aqueous solution of sodium bicarbonate was added to the residue
  6. extractionfollowed by extraction with chloroform
  7. washThe organic layer was washed with a saturated saline
  8. dry with materialdried over anhydrous magnesium sulfate
  9. distillationthe solvent was distilled off under reduced pressure
  10. customThe residue was purified by silica gel column chromatography (chloroform)

Sources & evidence

ORD record
ord-f082b766e91145e2b2b61cb397013e17
Source dataset
uspto-grants-2004_04
Patent number
US06716987B1

Reaction notes

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