Sodium Hydroxide → (5-Chloro-4-(5-fluoro-2-benzothiazolyl)amino-2-fluorophenyl)acetic acid

HRID 1372684Notes

Reaction equation

HRID 1372684 reaction equation
[Cl:1][C:2]1[C:3]([NH:15][C:16]2[S:17][C:18]3[CH:24]=[CH:23][C:22]([F:25])=[CH:21][C:19]=3[N:20]=2)=[CH:4][C:5]([F:14])=[C:6]([CH2:8][C:9]([O:11]CC)=[O:10])[CH:7]=1.[OH-].[Na+]>C1COCC1>[Cl:1][C:2]1[C:3]([NH:15][C:16]2[S:17][C:18]3[CH:24]=[CH:23][C:22]([F:25])=[CH:21][C:19]=3[N:20]=2)=[CH:4][C:5]([F:14])=[C:6]([CH2:8][C:9]([OH:11])=[O:10])[CH:7]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 58778765Ethyl (5-chloro-4-(5-fluoro-2-benzothiazolyl)amino-2-fluorophenyl)acetate

Product 1

HCID 17859016(5-Chloro-4-(5-fluoro-2-benzothiazolyl)amino-2-fluorophenyl)acetic acidYield 86%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Ethyl (5-chloro-4-(5-fluoro-2-benzothiazolyl)amino-2-fluorophenyl)acetate (298 mg, 0.78 mmol) was dissolved in THF (5 ml). To the resulting solution was added 0.5N NaOH (5.0 ml, 2.50 mmol). The resulting mixture was stirred at room temperature for 3 hours. The reaction mixture was poured in ice-1N HCl. The crystals thus precipitated were collected by filtration under reduced pressure, washed with water and dried under reduced pressure to give (5-chloro-4-(5-fluoro-2-benzothiazolyl)amino-2-fluorophenyl)acetic acid (237 mg, 86%) as a pale yellow 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-6eed12fa04614de5ba0408d49f072efe
Source dataset
uspto-grants-2007_01
Patent number
US07157487B2

Reaction notes

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