Sodium Hydroxide → (1-{1-[5-(4-Fluoro-phenyl)-2-methyl-thiazol-4-yl]-methanoyl}-piperidin-2-yl)-acetic acid

HRID 598544Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 598544
C[O:2][C:3](=[O:26])[CH2:4][CH:5]1[CH2:10][CH2:9][CH2:8][CH2:7][N:6]1[C:11]([C:13]1[N:14]=[C:15]([CH3:25])[S:16][C:17]=1[C:18]1[CH:23]=[CH:22][C:21]([F:24])=[CH:20][CH:19]=1)=[O:12].[OH-].[Na+]>CO.O>[F:24][C:21]1[CH:22]=[CH:23][C:18]([C:17]2[S:16][C:15]([CH3:25])=[N:14][C:13]=2[C:11]([N:6]2[CH2:7][CH2:8][CH2:9][CH2:10][CH:5]2[CH2:4][C:3]([OH:26])=[O:2])=[O:12])=[CH:19][CH:20]=1

Komponenten

4

Edukt 2

HCID 14798Sodium HydroxideHCID 66968203(1-{1-[5-(4-Fluoro-phenyl)-2-methyl-thiazol-4-yl]-methanoyl}-piperidin-2-yl)-acetic acid methyl ester

Produkt 1

HCID 23146320(1-{1-[5-(4-Fluoro-phenyl)-2-methyl-thiazol-4-yl]-methanoyl}-piperidin-2-yl)-acetic acidAusbeute 82 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 22242641Methanol--water (1/1)Lösungsmittel

Versuchsvorschrift

A stirring solution of (1-{1-[5-(4-Fluoro-phenyl)-2-methyl-thiazol-4-yl]-methanoyl}-piperidin-2-yl)-acetic acid methyl ester, D16 (4.00 g, 10.6 mmol) in methanol/water (75 ml/25 ml) was treated with sodium hydroxide (0.85 g, 21.3 mmol). The mixture was stirred for 16 h at room temperature. The methanol was removed in vacuo and the residue was diluted with water and extracted with diethyl ether (2×). The aqueous phase was acidified with 5N HCl and the product was extracted with ethyl acetate. The organic phase was dried (MgSO4) and the solvent removed in vacuo. The residue was triturated with pentane to afford the title compound as a white solid (3.10 g, 82%).

Aufarbeitung

  1. customThe methanol was removed in vacuo
  2. additionthe residue was diluted with water
  3. extractionextracted with diethyl ether (2×)
  4. extractionthe product was extracted with ethyl acetate
  5. dry with materialThe organic phase was dried (MgSO4)
  6. customthe solvent removed in vacuo
  7. customThe residue was triturated with pentane

Quellen und Nachweise

ORD-Eintrag
ord-2002a5e4b15a45a7b68110641e69c3a9
Quelldatensatz
uspto-grants-2011_03
Patentnummer
US07897618B2

Notizen zur Reaktion

Wird geladen…