Sodium Hydroxide → (2-(3-Fluoro-2-methylphenylamino)-7-fluoro-6-benzoxazolyl)acetic acid

HRID 1372649Notes

Reaction equation

HRID 1372649 reaction equation
[F:1][C:2]1[C:3]([CH3:24])=[C:4]([NH:8][C:9]2[O:10][C:11]3[C:17]([F:18])=[C:16]([CH2:19][C:20]([O:22]C)=[O:21])[CH:15]=[CH:14][C:12]=3[N:13]=2)[CH:5]=[CH:6][CH:7]=1.[OH-].[Na+]>C1COCC1.CO>[F:1][C:2]1[C:3]([CH3:24])=[C:4]([NH:8][C:9]2[O:10][C:11]3[C:17]([F:18])=[C:16]([CH2:19][C:20]([OH:22])=[O:21])[CH:15]=[CH:14][C:12]=3[N:13]=2)[CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 44607519Methyl (2-(3-fluoro-2-methylphenylamino)-7-fluoro-6-benzoxazolyl)acetate

Product 1

HCID 17859428(2-(3-Fluoro-2-methylphenylamino)-7-fluoro-6-benzoxazolyl)acetic acidYield 94.9%

Reagents, catalysts & solvents 1

HCID 21899815MeOH tetrahydrofuranSolvent

Procedure

In THF/methanol (2:1, 60 ml) was dissolved methyl (2-(3-fluoro-2-methylphenylamino)-7-fluoro-6-benzoxazolyl)acetate (1.21 g, 3.64 mmol). To the resulting solution was added 1N NaOH (20 ml). After stirring at room temperature for 17 hours, the reaction mixture was distilled under reduced pressure to remove the solvent. The residue was acidified with 1N HCl. The crystals thus precipitated were collected by filtration under reduced pressure, washed with water and dried under reduced pressure to give (2-(3-fluoro-2-methylphenylamino)-7-fluoro-6-benzoxazolyl)acetic acid (1.10 g, 15%) as a colorless solid.

Workup

  1. distillationthe reaction mixture was distilled under reduced pressure
  2. customto remove the solvent
  3. customThe crystals thus precipitated
  4. filtrationwere collected by filtration under reduced pressure
  5. washwashed with water
  6. customdried under reduced pressure

Sources & evidence

ORD record
ord-c78be33662c94cefbe94e26b241fcefb
Source dataset
uspto-grants-2007_01
Patent number
US07157487B2

Reaction notes

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