Sodium Hydroxide → (2-(5-Fluoro-2-methylphenylamino)-4-fluoro-6-benzoxazolyl)acetic acid

HRID 1372656Notes

Reaction equation

HRID 1372656 reaction equation
[F:1][C:2]1[CH:3]=[CH:4][C:5]([CH3:25])=[C:6]([NH:8][C:9]2[O:10][C:11]3[CH:17]=[C:16]([CH2:18][C:19]([O:21]CC)=[O:20])[CH:15]=[C:14]([F:24])[C:12]=3[N:13]=2)[CH:7]=1.[OH-].[Na+]>C1COCC1.CO.Cl>[F:1][C:2]1[CH:3]=[CH:4][C:5]([CH3:25])=[C:6]([NH:8][C:9]2[O:10][C:11]3[CH:17]=[C:16]([CH2:18][C:19]([OH:21])=[O:20])[CH:15]=[C:14]([F:24])[C:12]=3[N:13]=2)[CH:7]=1

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 58778879Ethyl (2-(5-fluoro-2-methylphenylamino)-4-fluoro-6-benzoxazolyl)acetate

Product 1

HCID 17858931(2-(5-Fluoro-2-methylphenylamino)-4-fluoro-6-benzoxazolyl)acetic acidYield 83.6%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 21899815MeOH tetrahydrofuranSolvent

Procedure

Ethyl (2-(5-fluoro-2-methylphenylamino)-4-fluoro-6-benzoxazolyl)acetate (215 mg, 0.62 mmol) was dissolved in THF/methanol (1/1, 20 ml). To the resulting solution was added 0.25N NaOH (12.4 ml, 3.10 mmol). The resulting mixture was stirred at room temperature for 1 hour. The reaction mixture was poured in 1N HCl to acidify the mixture, followed by extraction with chloroform/methanol (10/1). The extract was dried over anhydrous sodium sulfate, and distilled under reduced pressure to remove the solvent to give (2-(5-fluoro-2-methylphenylamino)-4-fluoro-6-benzoxazolyl)acetic acid (165 mg, 83%) as a pale brown solid.

Workup

  1. extractionfollowed by extraction with chloroform/methanol (10/1)
  2. dry with materialThe extract was dried over anhydrous sodium sulfate
  3. distillationdistilled under reduced pressure
  4. customto remove the solvent

Sources & evidence

ORD record
ord-80de7bea59664990964b0c064d5aaece
Source dataset
uspto-grants-2007_01
Patent number
US07157487B2

Reaction notes

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