Methanol → HCID 19434899, compound

HRID 1736189Notes

Reaction equation

HRID 1736189 reaction equation
[F:1][C:2]1[C:3]([CH2:35][O:36]S(C)(=O)=O)=[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].[CH3:41]O>>[F:1][C:2]1[C:3]([CH2:35][O:36][CH3:41])=[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

3

Reactant 2

HCID 887MethanolHCID 10721996HCID 10721996, compound

Product 1

HCID 19434899HCID 19434899, compoundYield 86%

Procedure

800 mg (1.37 mmol) of 6,8-difluoro-2-(3-fluoro-4-pivaloylaminophenyl)-7-methanesulfonyloxymethyl-5-pivaloylamino-4H-1-benzopyran-4-one obtained in Example 120 (1) was dissolved in 200 mL of methanol and the solution was heated at reflux for 24 hours. The solvent was distilled off under reduced pressure, the residue was dissolved in chloroform, washed 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:acetonitrile=20:1) to give 610 mg of 6,8-difluoro-2-(3-fluoro-4-pivaloylaminophenyl)-7-methoxymethyl-5-pivaloylamino-4H-1-benzopyran-4-one (yield: 86%).

Workup

  1. temperaturethe solution was heated
  2. temperatureat reflux for 24 hours
  3. distillationThe solvent was distilled off under reduced pressure
  4. dissolutionthe residue was dissolved in chloroform
  5. washwashed once with an aqueous saturated solution of sodium chloride
  6. dry with materialdried over anhydrous sodium sulfate
  7. distillationThe solvent was distilled off under reduced pressure
  8. customthe residue was purified by silica gel column chromatography (chloroform:acetonitrile=20:1)

Sources & evidence

ORD record
ord-41a99a4436274ac198f322c3dc7402bf
Source dataset
uspto-grants-1996_07
Patent number
US05539112

Reaction notes

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