m-Chloroperbenzoic acid → HCID 69156637, compound

HRID 750308Notes

Reaction equation

HRID 750308 reaction equation
[CH3:1][O:2][C:3]([C:5]1[N:6]([CH2:23][C:24]2[CH:29]=[CH:28][C:27]([CH2:30][S:31][C:32]3[CH:37]=[CH:36][C:35]([C:38]([O:40][CH3:41])=[O:39])=[CH:34][CH:33]=3)=[CH:26][CH:25]=2)[C:7](=[O:22])[C:8]2[C:13]([C:14]=1[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)=[CH:12][C:11]([Br:21])=[CH:10][CH:9]=2)=[O:4].ClC1C=CC=C(C(OO)=[O:50])C=1>ClCCl>[CH3:1][O:2][C:3]([C:5]1[N:6]([CH2:23][C:24]2[CH:29]=[CH:28][C:27]([CH2:30][S:31]([C:32]3[CH:33]=[CH:34][C:35]([C:38]([O:40][CH3:41])=[O:39])=[CH:36][CH:37]=3)=[O:50])=[CH:26][CH:25]=2)[C:7](=[O:22])[C:8]2[C:13]([C:14]=1[C:15]1[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=1)=[CH:12][C:11]([Br:21])=[CH:10][CH:9]=2)=[O:4]

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 69157787HCID 69157787, compound

Product 1

HCID 69156637HCID 69156637, compoundYield 49%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 6-bromo-2-[4-(4-methoxycarbonylphenylsulfanylmethyl)benzyl]-1-oxo-4-phenyl-1,2-dihydroisoquinoline-3-carboxylic acid methyl ester (189 mg) in dichloromethane (20 ml) was added 3-chloroperbenzoic acid (74 mg) under ice-cooling and the mixture was stirred under ice-cooling for 1 hr. The mixture was diluted with dichloromethane, washed with saturated aqueous sodium hydrogen carbonate solution and saturated 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=7/3→1/4) to give the title compound (95 mg, 49%).

Workup

  1. temperaturecooling
  2. temperaturecooling for 1 hr
  3. washwashed with saturated aqueous sodium hydrogen carbonate solution and saturated 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=7/3→1/4)

Sources & evidence

ORD record
ord-0b34b3c0b1324efaa3e2311b01509513
Source dataset
uspto-grants-2008_07
Patent number
US07402595B2

Reaction notes

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