HCID 19434836, compound → HCID 19434817, compound

HRID 1736167Notes

Reaction equation

HRID 1736167 reaction equation
[F:1][C:2]1[C:3]([CH:35]([OH:37])[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]>C1(C)C=CC=CC=1.[O-2].[O-2].[Mn+4]>[C:35]([C:3]1[C:2]([F:1])=[C:26]([NH:27][C:28](=[O:33])[C:29]([CH3:32])([CH3:31])[CH3:30])[C:6]2[C:7](=[O:25])[CH:8]=[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)[O:10][C:5]=2[C:4]=1[F:34])(=[O:37])[CH3:36]

Participants

4

Reactant 1

HCID 19434836HCID 19434836, compound

Product 1

HCID 19434817HCID 19434817, compoundYield 87.1%

Reagents, catalysts & solvents 2

HCID 178418406HCID 178418406, compoundCatalystHCID 1140TolueneSolvent

Procedure

206 mg (0.398 mmol) of 6,8-difluoro-2-(3-fluoro-4-pivaloylaminophenyl)-7-(1-hydroxyethyl)-5-pivaloylamino-4H-1-benzopyran-4-one obtained in Example 94 (1) was suspended in 20 mL of toluene, 348 mg (3.98 mmol) of manganese dioxide was added and the mixture was heated at reflux for 2 hours. The reaction solution was filtered, the solvent was distilled off under reduced pressure and the residue was purified by silica gel column chromatography (chloroform:acetonitrile=50:1) to give 179 mg of 7-acetyl-6,8-difluoro-2-(3-fluoro-4-pivaloylaminophenyl)-5-pivaloylamino-4H-1-benzopyran-4-one (yield: 87%).

Workup

  1. temperaturethe mixture was heated
  2. temperatureat reflux for 2 hours
  3. filtrationThe reaction solution was filtered
  4. distillationthe solvent was distilled off under reduced pressure
  5. customthe residue was purified by silica gel column chromatography (chloroform:acetonitrile=50:1)

Sources & evidence

ORD record
ord-7e7881a722f14873bfd80ce7e2f38b9a
Source dataset
uspto-grants-1996_07
Patent number
US05539112

Reaction notes

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