Water → HCID 59459707, compound

HRID 1712664Notes

Reaction equation

HRID 1712664 reaction equation
[CH2:1]([O:8][C:9]([C:11]1([C:14](=[O:33])[NH:15][C:16]2[CH:21]=[CH:20][C:19]([O:22][C:23]3[CH:28]=[CH:27][N:26]=[C:25](C(=O)N)[CH:24]=3)=[CH:18][C:17]=2[F:32])[CH2:13][CH2:12]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.O.C(O)(=O)C.C(O)(=O)C.IC1C=CC=CC=1.[OH-].[Na+].C[N:53]1CCCC1=O>C(OCC)(=O)C>[CH2:1]([O:8][C:9]([C:11]1([C:14](=[O:33])[NH:15][C:16]2[CH:21]=[CH:20][C:19]([O:22][C:23]3[CH:28]=[CH:27][N:26]=[C:25]([NH2:53])[CH:24]=3)=[CH:18][C:17]=2[F:32])[CH2:12][CH2:13]1)=[O:10])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

7

Reactant 5

HCID 962WaterHCID 13387N-methyl-2-pyrrolidoneHCID 14798Sodium HydroxideHCID 12217721Iodo benzene diacetateHCID 247884991-[4-(2-Carbamoylpyridin-4-yloxy)-2-fluorophenylcarbamoyl]cyclopropanecarboxylic acid benzyl ester

Product 1

HCID 59459707HCID 59459707, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

1-[4-(2-Carbamoylpyridin-4-yloxy)-2-fluorophenylcarbamoyl]cyclopropanecarboxylic acid benzyl ester (17.9 g) was dissolved in N-methyl-2-pyrrolidone (125 ml) at room temperature, and water (7.2 ml) was added. Iodobenzene diacetate (14.1 g) was added with stirring at room temperature, followed by stirring for 4 hours and 7 minutes. Ethyl acetate (268 ml) and a 1N aqueous solution of sodium hydroxide (179 ml) were added to the reaction mixture, and the layers were separated. The organic layer was washed with a 5% aqueous solution of sodium chloride (179 ml) three times and water (179 ml) once, dried over magnesium sulfate, filtered, and concentrated. Toluene (72 ml) was added to the resultant crystals, and the mixture was heated and stirred at 90° C. After confirming the crystals were dissolved, the mixture was allowed to cool down to room temperature. The precipitated crystals were collected by filtration, washed with toluene (18 ml), and dried under reduced pressure at 50° C. for 4 hours to give the title compound (11.9 g) as pale orange crystals.

Workup

  1. stirringby stirring for 4 hours and 7 minutes
  2. customthe layers were separated
  3. washThe organic layer was washed with a 5% aqueous solution of sodium chloride (179 ml) three times and water (179 ml) once
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. additionToluene (72 ml) was added to the resultant crystals
  8. temperaturethe mixture was heated
  9. stirringstirred at 90° C
  10. dissolutionwere dissolved
  11. temperatureto cool down to room temperature
  12. filtrationThe precipitated crystals were collected by filtration
  13. washwashed with toluene (18 ml)
  14. customdried under reduced pressure at 50° C. for 4 hours

Sources & evidence

ORD record
ord-3fc3029a68674cc19eb4aa90e8189570
Source dataset
uspto-grants-2010_09
Patent number
US07790885B2

Reaction notes

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