Bicyclo[2.2.1]heptane-1-methanesulfonic acid, 7,7-dimethyl-2-oxo-, (1S)- → HCID 18673945, compound

HRID 1635997Notes

Reaction equation

HRID 1635997 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:25]=[CH:26][C:27]=1[Cl:28])[C:5]([NH:7][C:8]1[CH:9]=[N:10][C:11]([O:14][C:15]2[CH:23]=[CH:22][CH:21]=[C:20]3[C:16]=2[CH2:17][CH2:18][C:19]3=[O:24])=[CH:12][CH:13]=1)=[O:6].C([O-])([O-])O[CH2:31][CH3:32].C12(CS(O)(=O)=O)C(C)(C)C(CC1)CC2=O>C(O)C>[Cl:1][C:2]1[CH:3]=[C:4]([CH:25]=[CH:26][C:27]=1[Cl:28])[C:5]([NH:7][C:8]1[CH:9]=[N:10][C:11]([O:14][C:15]2[CH:23]=[CH:22][CH:21]=[C:20]3[C:16]=2[CH2:17][CH:18]=[C:19]3[O:24][CH2:31][CH3:32])=[CH:12][CH:13]=1)=[O:6]

Participants

5

Reactant 3

HCID 18462Bicyclo[2.2.1]heptane-1-methanesulfonic acid, 7,7-dimethyl-2-oxo-, (1S)-HCID 9909644HCID 9909644, compoundHCID 53630039Ethylorthoformate

Product 1

HCID 18673945HCID 18673945, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

3.5 g of 3,4-dichloro-N1-{6-(1-oxo-2,3-dihydro-1H-inden-4-yl)oxy]-3-pyridinyl}benzamide obtained in Example 1 was suspended in 140 ml of ethanol. To the suspension, 14 ml of ethyl orthoformate, 820 mg of (±)-10-camphorsulfonic acid and 3.5 g of 4A molecular sieves were added and the mixture was heated at reflux for 30 minutes. After air cooling, the reaction mixture was filtered. To the filtrate, 8.5 ml of an aqueous 1N sodium hydroxide solution was added and the solvent was distilled off under reduced pressure. To the resulting residue, 100 ml of ethyl acetate was added and the solution was washed in turn with water and a saturated sodium hydrogencarbonate solution and then dried over magnesium sulfate. After drying, the solvent was distilled off and the resulting residue was purified by silica gel column chromatography (eluent: hexane/ethyl acetate (4:1)) to obtain the titled compound (white powder, 530 mg).

Workup

  1. temperaturethe mixture was heated
  2. temperatureat reflux for 30 minutes
  3. temperatureAfter air cooling
  4. filtrationthe reaction mixture was filtered
  5. additionTo the filtrate, 8.5 ml of an aqueous 1N sodium hydroxide solution was added
  6. distillationthe solvent was distilled off under reduced pressure
  7. additionTo the resulting residue, 100 ml of ethyl acetate was added
  8. washthe solution was washed in turn with water
  9. dry with materiala saturated sodium hydrogencarbonate solution and then dried over magnesium sulfate
  10. customAfter drying
  11. distillationthe solvent was distilled off
  12. customthe resulting residue was purified by silica gel column chromatography (eluent: hexane/ethyl acetate (4:1))

Sources & evidence

ORD record
ord-857f07bfca1e465ea0df96793457afb9
Source dataset
uspto-grants-2003_01
Patent number
US06511995B1

Reaction notes

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