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

HRID 1372708

Reaktionsgleichung

Reaktionsgleichung von HRID 1372708
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

Komponenten

5

Edukt 3

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

Produkt 1

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

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 313Hydrochloric AcidLösungsmittel

Versuchsvorschrift

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.

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-d34fa89d6d9a42f9932a5d19f62f30cb
Quelldatensatz
uspto-grants-2007_01
Patentnummer
US07157487B2

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