Sodium Hydroxide → (5-Chloro-2-fluoro-4-(((5-fluoro-1-methyl-3-indolyl)carbonyl)amino)phenyl)acetic acid

HRID 1372708

Reaction equation

HRID 1372708 reaction equation
C1COCC1.CO.[OH-].[Na+].[Cl:10][C:11]1[C:12]([NH:24][C:25]([C:27]2[C:35]3[C:30](=[CH:31][CH:32]=[C:33]([F:36])[CH:34]=3)[N:29]([CH3:37])[CH:28]=2)=[O:26])=[CH:13][C:14]([F:23])=[C:15]([CH2:17][C:18]([O:20]CC)=[O:19])[CH:16]=1>Cl>[Cl:10][C:11]1[C:12]([NH:24][C:25]([C:27]2[C:35]3[C:30](=[CH:31][CH:32]=[C:33]([F:36])[CH:34]=3)[N:29]([CH3:37])[CH:28]=2)=[O:26])=[CH:13][C:14]([F:23])=[C:15]([CH2:17][C:18]([OH:20])=[O:19])[CH:16]=1

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 21899815MeOH tetrahydrofuranHCID 58778397Ethyl (5-chloro-2-fluoro-4-(((5-fluoro-1-methyl-3-indolyl)carbonyl)amino)phenyl)acetate

Product 1

HCID 17858826(5-Chloro-2-fluoro-4-(((5-fluoro-1-methyl-3-indolyl)carbonyl)amino)phenyl)acetic acidYield 91%

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

THF/methanol (1/1, 60 ml) and 0.25N NaOH (43 ml, 10.6 mmol) were added to ethyl (5-chloro-2-fluoro-4-(((5-fluoro-1-methyl-3-indolyl)carbonyl)amino)phenyl)acetate (865 mmol, 2.13 mmol) and the mixture was stirred at room temperature for 3 hours. The reaction mixture was poured in 1N HCl, followed by extraction with a chloroform/methanol (10/1) mixture. The extract was dried over anhydrous sodium sulfate, and distilled under reduced pressure to remove the solvent. The residue was solidified with methanol/chloroform/hexane. The crystals thus precipitated were collected by filtration under reduced pressure and dried under reduced pressure to give (5-chloro-2-fluoro-4-(((5-fluoro-1-methyl-3-indolyl)carbonyl)amino)phenyl)acetic acid (736 mg, 91%) as a white crystalline powder.

Workup

  1. extractionfollowed by extraction with a chloroform/methanol (10/1) mixture
  2. dry with materialThe extract was dried over anhydrous sodium sulfate
  3. distillationdistilled under reduced pressure
  4. customto remove the solvent
  5. customThe crystals thus precipitated
  6. filtrationwere collected by filtration under reduced pressure
  7. customdried under reduced pressure

Sources & evidence

ORD record
ord-d34fa89d6d9a42f9932a5d19f62f30cb
Source dataset
uspto-grants-2007_01
Patent number
US07157487B2

Linked notes

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