Sodium Hydroxide → 3-[4-(4-Fluorophenyl)-1,3-thiazol-2-yl]propanoic acid

HRID 1397302Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1397302
[OH-].[Na+].[F:3][C:4]1[CH:9]=[CH:8][C:7]([C:10]2[N:11]=[C:12]([CH2:15][CH2:16][C:17]([O:19]CC)=[O:18])[S:13][CH:14]=2)=[CH:6][CH:5]=1>CO>[F:3][C:4]1[CH:5]=[CH:6][C:7]([C:10]2[N:11]=[C:12]([CH2:15][CH2:16][C:17]([OH:19])=[O:18])[S:13][CH:14]=2)=[CH:8][CH:9]=1

Komponenten

4

Edukt 2

HCID 14798Sodium HydroxideHCID 67324988Ethyl 3-(4-(4-fluorophenyl)thiazol-2-yl)propanoate

Produkt 1

HCID 393539643-[4-(4-Fluorophenyl)-1,3-thiazol-2-yl]propanoic acidAusbeute 79,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Versuchsvorschrift

1N NaOH (5 mL) was added to an ice-cooled solution of crude ethyl 3-(4-(4-fluorophenyl)thiazol-2-yl)propanoate (450 mg, 1.61 mmol) in MeOH (5 mL) and the solution was allowed to stir at room temperature for 1 h. Solvent was evaporated and the reaction mixture was diluted with water. The aqueous layer was washed with EtOAc and the pH of the aqueous solution was adjusted to ˜2 using 1N HCl. The organic product was extracted with EtOAc and the organic layer was dried over anhydrous sodium sulfate and concentrated under reduced pressure to yield 3-(4-(4-fluorophenyl)thiazol-2-yl)propanoic acid (320 mg, yield 79%) as a white solid. 1H NMR (300 MHz, DMSO-d6) δ 12.29 (br s, 1H), 7.99-7.96 (m, 2H), 7.93 (s, 1H), 7.28-7.22 (t, J=9.0 Hz, 2H), 3.25-3.20 (t, J=7.1 Hz, 2H), 2.78-2.74 (t, J=7.1 Hz, 2H). MS (ESI) m/z: Calculated for C12H10FNO2S: 251.04. found: 252.2 (M+H)+.

Aufarbeitung

  1. customSolvent was evaporated
  2. additionthe reaction mixture was diluted with water
  3. washThe aqueous layer was washed with EtOAc
  4. extractionThe organic product was extracted with EtOAc
  5. dry with materialthe organic layer was dried over anhydrous sodium sulfate
  6. concentrationconcentrated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-6e40b7e4e2fb4080a6be832fcc7929fb
Quelldatensatz
uspto-grants-2014_12
Patentnummer
US08901156B2

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