Sodium Hydroxide → HCID 135442650, compound

HRID 2111023Notes

Reaction equation

HRID 2111023 reaction equation
C([O:4][C:5]1[CH:10]=[CH:9][C:8]([C:11]2[C:15]([NH:16][C:17]([O:19][CH:20]([C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=3[Cl:28])[CH3:21])=[O:18])=[CH:14][O:13][N:12]=2)=[CH:7][CH:6]=1)(=O)C.[OH-].[Na+]>O1CCCC1>[OH:4][C:5]1[CH:6]=[CH:7][C:8]([C:11]2[C:15]([NH:16][C:17](=[O:18])[O:19][CH:20]([C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=3[Cl:28])[CH3:21])=[CH:14][O:13][N:12]=2)=[CH:9][CH:10]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 11475090HCID 11475090, compound

Product 1

HCID 135442650HCID 135442650, compoundYield 96.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution (20 ml) of 4-[4-({[1-(2-chlorophenyl)ethoxy]carbonyl}amino)-3-isoxazolyl]phenyl acetate (2.11 g, 5.26 mmol) in tetrahydrofuran was added 1M aqueous sodium hydroxide solution (7.0 ml), and the mixture was stirred at room temperature for 7 hours. The reaction mixture was concentrated under reduced pressure, and water was added. The mixture was neutralized with 1M hydrochloric acid and extracted with ethyl acetate. The organic layer was washed with saturated brine and dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure to give the title compound (1.82 g, 96%).

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure, and water
  2. additionwas added
  3. extractionextracted with ethyl acetate
  4. washThe organic layer was washed with saturated brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. customThe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-49f11a1f074d4d20b833e5b465f68db4
Source dataset
uspto-grants-2009_04
Patent number
US07517996B2

Reaction notes

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