Hydrochloric Acid → 4-[2-(Trifluoromethyl)phenoxy]piperidin-1-yl-1,3-thiazole-5-carboxylic acid

HRID 561199Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 561199
[F:1][C:2]([F:26])([F:25])[C:3]1[CH:24]=[CH:23][CH:22]=[CH:21][C:4]=1[O:5][CH:6]1[CH2:11][CH2:10][N:9]([C:12]2[S:13][C:14]([C:17]([O:19]C)=[O:18])=[CH:15][N:16]=2)[CH2:8][CH2:7]1.[OH-].[Na+].Cl>C1COCC1.CO>[F:25][C:2]([F:1])([F:26])[C:3]1[CH:24]=[CH:23][CH:22]=[CH:21][C:4]=1[O:5][CH:6]1[CH2:7][CH2:8][N:9]([C:12]2[S:13][C:14]([C:17]([OH:19])=[O:18])=[CH:15][N:16]=2)[CH2:10][CH2:11]1

Komponenten

5

Edukt 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 57659049Methyl 2-{4-[2-(trifluoromethyl)phenoxy]piperidin-1-yl}-1,3-thiazole-5-carboxylate

Produkt 1

HCID 666968024-[2-(Trifluoromethyl)phenoxy]piperidin-1-yl-1,3-thiazole-5-carboxylic acid

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 21899815MeOH tetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

A mixture of methyl 2-{4-[2-(trifluoromethyl)phenoxy]piperidin-1-yl}-1,3-thiazole-5-carboxylate (16 g, 41.4 mmol) and 1 N NaOH (85 mL, 85 mmol) in THF/MeOH (1:1) (v/v) (300 mL) was heated at 80° C. bath for 1 h. Volatile solvents were removed in vacuo. The residue was diluted with H2O, acidified with 1 N HCl (2.2 equiv) and extracted with EtOAc. The EtOAc extract was washed with H2O, dried (Na2SO4) and concentrated to give the title compound as a white solid.

Aufarbeitung

  1. customVolatile solvents were removed in vacuo
  2. additionThe residue was diluted with H2O
  3. extractionextracted with EtOAc
  4. extractionThe EtOAc extract
  5. washwas washed with H2O
  6. dry with materialdried (Na2SO4)
  7. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-82c9c5910d8c4eac8e307bfd800dbac3
Quelldatensatz
uspto-grants-2011_11
Patentnummer
US08063224B2

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