Sodium Hydroxide → 2-(4-((Tert-butoxycarbonyl)amino)phenyl)acetic acid

HRID 547448Notes

Reaction equation

HRID 547448 reaction equation
C([O:3][C:4](=[O:20])[CH2:5][C:6]1[CH:11]=[CH:10][C:9]([NH:12][C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])=[CH:8][CH:7]=1)C.[OH-].[Na+]>CO>[C:16]([O:15][C:13]([NH:12][C:9]1[CH:8]=[CH:7][C:6]([CH2:5][C:4]([OH:20])=[O:3])=[CH:11][CH:10]=1)=[O:14])([CH3:19])([CH3:17])[CH3:18]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 86719106HCID 86719106, compound

Product 1

HCID 28249932-(4-((Tert-butoxycarbonyl)amino)phenyl)acetic acidYield 63.5%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To 20 mL of a methanol solution containing 0.7 g of ethyl-4-tert-butoxycarbonylaminophenylacetate, 13 mL of 1M aqueous sodium hydroxide solution was added and stirred at room temperature for a day and night. The reaction liquid was concentrated under reduced pressure, and rendered acidic with 2M aqueous citric acid solution. The precipitated crystal was recovered by filtration under cooling with ice, to provide 0.40 g of 4-t-butoxycarbonylaminophenylacetic acid as pale yellow crystal. The compound was dissolved in 13 mL of THF, and to which 0.40 g of CDI was added, followed by 2 hours' stirring at room temperature. Then 13 mL of a THF solution containing 0.71 g of DBU and 0.26 g of 5-amino-3-(4-fluorophenyl)-4-pyrimidinylisoxazole were added and stirred for a night at room temperature. The solvent was distilled off of the reaction solution under reduced pressure and water was added to the residue, followed by extraction with ethyl acetate. The ethyl acetate extract was dried over anhydrous magnesium sulfate and removed of the solvent by distillation under reduced pressure. The residue was purified on 30 g silica gel chromatography (eluent, chloroform:methanol=100:1), and the crystalline residue was washed with ether-hexane to provide 0.364 g (yield: 46%) of the title compound.

Workup

  1. additionwas added
  2. customThe reaction liquid
  3. concentrationwas concentrated under reduced pressure
  4. filtrationThe precipitated crystal was recovered by filtration
  5. temperatureunder cooling with ice

Sources & evidence

ORD record
ord-777c28b6600f4849a703283e625a4aac
Source dataset
uspto-grants-2011_05
Patent number
US07939536B2

Reaction notes

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