Sodium Hydroxide → 2-(2-(1-tert-butyl-5-(4-fluorophenyl)-1H-pyrazol-4-yl)thiazol-4-yl)acetic acid

HRID 1750344Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1750344
[C:1]([N:5]1[C:9]([C:10]2[CH:15]=[CH:14][C:13]([F:16])=[CH:12][CH:11]=2)=[C:8]([C:17]2[S:18][CH:19]=[C:20]([CH2:22][C:23]([O:25]CC)=[O:24])[N:21]=2)[CH:7]=[N:6]1)([CH3:4])([CH3:3])[CH3:2].[OH-].[Na+]>C(O)C>[C:1]([N:5]1[C:9]([C:10]2[CH:11]=[CH:12][C:13]([F:16])=[CH:14][CH:15]=2)=[C:8]([C:17]2[S:18][CH:19]=[C:20]([CH2:22][C:23]([OH:25])=[O:24])[N:21]=2)[CH:7]=[N:6]1)([CH3:4])([CH3:2])[CH3:3]

Komponenten

4

Edukt 2

HCID 14798Sodium Hydroxide2×HCID 86721181ethyl 2-(2-(1-tert-butyl-5-(4-fluorophenyl)-1H-pyrazol-4-yl)thiazol-4-yl)acetate

Produkt 1

HCID 867211822-(2-(1-tert-butyl-5-(4-fluorophenyl)-1H-pyrazol-4-yl)thiazol-4-yl)acetic acidAusbeute 69 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

A solution of the compound (3.96 g, 10.22 mmol) obtained in step 5 and 1N aqueous sodium hydroxide solution (15.33 mL, 15.33 mmol) in ethanol (50 mL) was stirred at room temperature for 2 hr. To the reaction mixture was further added 1N aqueous sodium hydroxide solution (5.0 mL, 5.0 mmol), and the mixture was stirred at room temperature for 30 min. The reaction mixture was concentrated under reduced pressure, and water was added to the residue. 1N Hydrochloric acid was added thereto, and the precipitate was collected by filtration, and crystallized from ethyl acetate and hexane to give 2-(2-(1-tert-butyl-5-(4-fluorophenyl)-1H-pyrazol-4-yl)thiazol-4-yl)acetic acid (2.52 g, 7.01 mmol, 69%) as a pale-yellow powder.

Aufarbeitung

  1. concentrationThe reaction mixture was concentrated under reduced pressure, and water
  2. additionwas added to the residue
  3. addition1N Hydrochloric acid was added
  4. filtrationthe precipitate was collected by filtration
  5. customcrystallized from ethyl acetate and hexane

Quellen und Nachweise

ORD-Eintrag
ord-671b703e31404410880b8625a0a09735
Quelldatensatz
uspto-grants-2015_10
Patentnummer
US09156837B2

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