Hydrochloric Acid → 4-({5-Chloro-6-[(3,3-difluorocyclobutyl)methoxy]pyridin-3-yl}oxy)-2,5-difluorobenzoic acid

HRID 2048039Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2048039
[Cl:1][C:2]1[CH:3]=[C:4]([O:16][C:17]2[C:29]([F:30])=[CH:28][C:20]([C:21]([O:23]C(C)(C)C)=[O:22])=[C:19]([F:31])[CH:18]=2)[CH:5]=[N:6][C:7]=1[O:8][CH2:9][CH:10]1[CH2:13][C:12]([F:15])([F:14])[CH2:11]1.[OH-].[Na+].Cl>C1COCC1.CO>[Cl:1][C:2]1[CH:3]=[C:4]([O:16][C:17]2[C:29]([F:30])=[CH:28][C:20]([C:21]([OH:23])=[O:22])=[C:19]([F:31])[CH:18]=2)[CH:5]=[N:6][C:7]=1[O:8][CH2:9][CH:10]1[CH2:11][C:12]([F:14])([F:15])[CH2:13]1

Komponenten

6

Edukt 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 58042465tert-Butyl 4-({5-chloro-6-[(3,3-difluorocyclobutyl)methoxy]pyridin-3-yl}oxy)-2,5-difluorobenzoate

Produkt 1

HCID 580424074-({5-Chloro-6-[(3,3-difluorocyclobutyl)methoxy]pyridin-3-yl}oxy)-2,5-difluorobenzoic acidAusbeute 88 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 887MethanolLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

tert-Butyl 4-({5-chloro-6-[(3,3-difluorocyclobutyl)methoxy]pyridin-3-yl}oxy)-2,5-difluorobenzoate (Preparation 7, 0.400 g, 0.87 mmol) was dissolved in THF (5.0 mL) and methanol (5.0 mL). Then an aqueous solution of sodium hydroxide was added (3.0 M, 5.0 mL) and the mixture was stirred at room temperature under nitrogen for 3 hours. Aqueous solution of HCl (1.0 M, 75.0 mL) was added and the mixture was extracted with EtOAc (100 mL). The organic layer was dried over sodium sulfate, filtered, and concentrated in vacuo. The residue was purified by reverse phase preparative HPLC (trilution method) to afford the title compound (0.31 g, 88%):

Aufarbeitung

  1. extractionthe mixture was extracted with EtOAc (100 mL)
  2. dry with materialThe organic layer was dried over sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. customThe residue was purified by reverse phase preparative HPLC (trilution method)

Quellen und Nachweise

ORD-Eintrag
ord-e70616b5e7934b2bb64b8b722e4ba517
Quelldatensatz
uspto-grants-2013_11
Patentnummer
US08592629B2

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