m-Chloroperbenzoic acid → HCID 10769055, compound

HRID 1736160Notes

Reaction equation

HRID 1736160 reaction equation
[F:1][C:2]1[C:3](SC)=[C:4]([F:34])[C:5]2[O:10][C:9]([C:11]3[CH:16]=[CH:15][C:14]([NH:17][C:18](=[O:23])[C:19]([CH3:22])([CH3:21])[CH3:20])=[C:13]([F:24])[CH:12]=3)=[CH:8][C:7](=[O:25])[C:6]=2[C:26]=1[NH:27][C:28](=[O:33])[C:29]([CH3:32])([CH3:31])[CH3:30].Cl[C:38]1C=CC=C(C(OO)=O)C=1.[S:48]([O-:51])(O)=[O:49].[Na+]>ClCCl>[F:1][C:2]1[C:3]([S:48]([CH3:38])(=[O:51])=[O:49])=[C:4]([F:34])[C:5]2[O:10][C:9]([C:11]3[CH:16]=[CH:15][C:14]([NH:17][C:18](=[O:23])[C:19]([CH3:22])([CH3:21])[CH3:20])=[C:13]([F:24])[CH:12]=3)=[CH:8][C:7](=[O:25])[C:6]=2[C:26]=1[NH:27][C:28](=[O:33])[C:29]([CH3:32])([CH3:31])[CH3:30]

Participants

5

Reactant 3

HCID 70297m-Chloroperbenzoic acidHCID 10649631HCID 10649631, compoundHCID 23665763Sodium Bisulfite

Product 1

HCID 10769055HCID 10769055, compoundYield 94%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

203 mg (0.391mmol) of 6,8-difluoro-2-(3-fluoro-4-pivaloylaminophenyl)-7-methylthio-5-pivaloylamino-4H-1-benzopyran-4-one obtained in Example 85 (2) was dissolved in 5 mL of dichloromethane, 850 mg (3.91 mmol) of m-chloroperbenzoic acid was added under ice-cooling and the mixture was stirred at room temperature for 3 hours. An aqueous solution of sodium hydrogensulfite was added to the reaction solution and the mixture was extracted once with chloroform. The organic layer was washed once with an aqueous solution of sodium bicarbonate, once with water and once with an aqueous saturated solution of sodium chloride and dried over anhydrous sodium sulfate. The solvent was distilled off under reduced pressure and the residue was purified by silica gel column chromatography (chloroform:ethyl acetate=40:l) to give 204 mg of 6,8-difluoro-2-(3-fluoro-4-pivaloylaminophenyl)-7-methylsulfonyl-5-pivaloylamino-4H-1-benzopyran-4-one (yield: 94%).

Workup

  1. temperaturecooling
  2. extractionthe mixture was extracted once with chloroform
  3. washThe organic layer was washed once with an aqueous solution of sodium bicarbonate, once with water and once with an aqueous saturated solution of sodium chloride
  4. dry with materialdried over anhydrous sodium sulfate
  5. distillationThe solvent was distilled off under reduced pressure
  6. customthe residue was purified by silica gel column chromatography (chloroform:ethyl acetate=40:l)

Sources & evidence

ORD record
ord-1b021e9b67fa467198c2fdbd13cc62d9
Source dataset
uspto-grants-1996_07
Patent number
US05539112

Reaction notes

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