p-Toluenesulfonic acid monohydrate → HCID 23060900, compound

HRID 750375Notes

Reaction equation

HRID 750375 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[C:8](=[O:12])[N:7]([CH2:13][C:14]1[CH:19]=[CH:18][C:17]([S:20]([CH2:23][CH2:24][CH2:25][O:26]C3CCCCO3)(=[O:22])=[O:21])=[CH:16][CH:15]=1)[C:6]([C:33](=[O:36])[CH2:34][CH3:35])=[C:5]2[C:37]1[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=1.O.C1(C)C=CC(S(O)(=O)=O)=CC=1>CO>[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[C:8](=[O:12])[N:7]([CH2:13][C:14]1[CH:15]=[CH:16][C:17]([S:20]([CH2:23][CH2:24][CH2:25][OH:26])(=[O:21])=[O:22])=[CH:18][CH:19]=1)[C:6]([C:33](=[O:36])[CH2:34][CH3:35])=[C:5]2[C:37]1[CH:38]=[CH:39][CH:40]=[CH:41][CH:42]=1

Participants

4

Reactant 2

HCID 521998p-Toluenesulfonic acid monohydrateHCID 23060967HCID 23060967, compound

Product 1

HCID 23060900HCID 23060900, compoundYield 99.1%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 6-bromo-4-phenyl-3-propionyl-2-[4-[3-(tetrahydropyran-2-yloxy)propan-1-sulfonyl]benzyl]-2H-isoquinolin-1-one (110 mg) in methanol (10 ml) was added p-toluenesulfonic acid monohydrate (49 mg), and the mixture was stirred at room temperature for 1 hr. The solvent was evaporated under reduced pressure and the residue was partitioned between ethyl acetate and 1N aqueous sodium hydroxide solution. The organic layer was washed with brine and dried by adding sodium sulfate. The solvent was evaporated under reduced pressure and the obtained residue was purified by silica gel column chromatography (n-hexane/ethyl acetate=3/2-+1/9) to give the title compound (95 mg, 98%).

Workup

  1. customThe solvent was evaporated under reduced pressure
  2. customthe residue was partitioned between ethyl acetate and 1N aqueous sodium hydroxide solution
  3. washThe organic layer was washed with brine
  4. customdried
  5. additionby adding sodium sulfate
  6. customThe solvent was evaporated under reduced pressure
  7. customthe obtained residue was purified by silica gel column chromatography (n-hexane/ethyl acetate=3/2-+1/9

Sources & evidence

ORD record
ord-759acab156e04188ba56e6db07da502b
Source dataset
uspto-grants-2008_07
Patent number
US07402595B2

Reaction notes

Loading…