Sodium Hydroxide → HCID 17858977, compound

HRID 1372770Notes

Reaction equation

HRID 1372770 reaction equation
[N:1]1([C:10]2[O:11][C:12]3[CH:18]=[C:17]([CH2:19][C:20]([O:22]C)=[O:21])[CH:16]=[CH:15][C:13]=3[N:14]=2)[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH2:3][CH2:2]1.[OH-].[Na+]>C1COCC1.CO>[N:1]1([C:10]2[O:11][C:12]3[CH:18]=[C:17]([CH2:19][C:20]([OH:22])=[O:21])[CH:16]=[CH:15][C:13]=3[N:14]=2)[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH2:3][CH2:2]1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 58778615HCID 58778615, compound

Product 1

HCID 17858977HCID 17858977, compoundYield 84.3%

Reagents, catalysts & solvents 1

HCID 21899815MeOH tetrahydrofuranSolvent

Procedure

To methyl (2-(1-indolinyl)-6-benzoxazolyl)acetate (200 mg, 0.649 mmol) were added THF/methanol (6/3 ml) and 1N NaOH (3 ml). The resulting mixture was stirred at room temperature for 1.5 hours. The reaction mixture was distilled under reduced pressure to remove the solvent. To the residue was added 1N HCl to acidify the residue therewith. The crystals thus precipitated were collected by filtration under reduced pressure, washed with water and dried under reduced pressure to give (2-(1-indolinyl)-6-benzoxazolyl)acetic acid (161 mg, 84%) as a brown solid.

Workup

  1. distillationThe reaction mixture was distilled under reduced pressure
  2. customto remove the solvent
  3. additionTo the residue was added 1N HCl
  4. customThe crystals thus precipitated
  5. filtrationwere collected by filtration under reduced pressure
  6. washwashed with water
  7. customdried under reduced pressure

Sources & evidence

ORD record
ord-f505e0b4a7ed462883e56cb2b17017a3
Source dataset
uspto-grants-2007_01
Patent number
US07157487B2

Reaction notes

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