Sodium Hydroxide → (4-(2-Benzoxazolyl)amino-5-chloro-2-fluorophenyl)acetic acid

HRID 1372669

Reaction equation

HRID 1372669 reaction equation
[O:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1[NH:10][C:11]1[C:16]([Cl:17])=[CH:15][C:14]([CH2:18][C:19]([O:21]CC)=[O:20])=[C:13]([F:24])[CH:12]=1.[OH-].[Na+]>C1COCC1>[O:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1[NH:10][C:11]1[C:16]([Cl:17])=[CH:15][C:14]([CH2:18][C:19]([OH:21])=[O:20])=[C:13]([F:24])[CH:12]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 58778947Ethyl (4-(2-benzoxazolyl)amino-5-chloro-2-fluorophenyl)acetate

Product 1

HCID 17858898(4-(2-Benzoxazolyl)amino-5-chloro-2-fluorophenyl)acetic acidYield 95.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Ethyl (4-(2-benzoxazolyl)amino-5-chloro-2-fluorophenyl)acetate (570 mg, 1.63 mmol) was dissolved in THF (5 ml). To the resulting solution was added 1N NaOH (5.0 ml, 5.00 mmol), followed by stirring at room temperature for 20 hours. The reaction mixture was poured in ice-1N HCl to acidify therewith. The crystals thus precipitated were collected by filtration under reduced pressure, washed with water and dried under reduced pressure to give (4-(2-benzoxazolyl)amino-5-chloro-2-fluorophenyl)acetic acid (497 mg, 95%) as a brown solid.

Workup

  1. customThe crystals thus precipitated
  2. filtrationwere collected by filtration under reduced pressure
  3. washwashed with water
  4. customdried under reduced pressure

Sources & evidence

ORD record
ord-8fe22556ae8f47298512c65b54a86b66
Source dataset
uspto-grants-2007_01
Patent number
US07157487B2

Linked notes

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