m-Chloroperbenzoic acid → HCID 10840071, compound

HRID 1736159Notes

Reaction equation

HRID 1736159 reaction equation
[F:1][C:2]1[C:3]([S:35][CH3:36])=[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].ClC1C=CC=C(C(OO)=[O:45])C=1.S([O-])(O)=O.[Na+]>ClCCl>[F:1][C:2]1[C:3]([S:35]([CH3:36])=[O:45])=[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]([CH3:30])([CH3:32])[CH3:31]

Participants

5

Reactant 3

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

Product 1

HCID 10840071HCID 10840071, compoundYield 95.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

204 mg (0.392mmol) of 6,8-difluoro-2-(3-fluoro-4-pivaloylaminophenyl)-7-methylthio-5-pivaloyiamino-4H-1-benzopyran-4-one obtained in Example 85 (2) was dissolved in 5 mL of dichloromethane, 86 mg (0.39 mmol) of m-chloroperbenzoic acid was added under ice-cooling and the mixture was stirred at the same temperature for2 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:methanol=100:1) to give 200 mg of 6,8-difluoro-2-(3-fluoro-4-pivaloylaminophenyl)-7-methylsulfinyl-5-pivaloylamino-4H-1-benzopyran-4-one (yield: 95%).

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:methanol=100:1)

Sources & evidence

ORD record
ord-a5fd65e71ec54d8c9444097f3e7e5df4
Source dataset
uspto-grants-1996_07
Patent number
US05539112

Reaction notes

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