Reaktion #595276

Reaktionsgleichung

hydrochloric acid

ethyl 3-{2-fluoro-4-[(4-{1-[(4-phenyl-1,3-thiazol-2-yl)methyl]butyl}benzyl)amino]phenyl}propanoate

tetrahydrofuran

lithium hydroxide monohydrate

→

title compound

Ausbeute 83.1%

3-{2-fluoro-4-[(4-{1-[(4-phenyl-1,3-thiazol-2-yl)methyl]butyl}benzyl)amino]phenyl}propanoic acid

Ausbeute 83.1%

Lösungsmittel

ethanol

water

Reaktionsbedingungen

Aufarbeitung

1. 1
   Extraktionextracted with ethyl acetate
2. 2
   WaschenThe organic layer was washed with saturated brine
3. 3
   Trocknendried over anhydrous magnesium sulfate
4. 4
   Einengenconcentrated under reduced pressure
5. 5
   SonstigeThe residue was purified by silica gel column chromatography (15%-60% ethyl acetate/hexane)

Vorschrift

To a solution of ethyl 3-{2-fluoro-4-[(4-{1-[(4-phenyl-1,3-thiazol-2-yl)methyl]butyl}benzyl)amino]phenyl}propanoate (0.420 g, 0.790 mmol) in a mixture of ethanol (6 mL), tetrahydrofuran (12 mL) and water (6 mL) was added lithium hydroxide monohydrate (0.198 g, 4.74 mmol), and the mixture was stirred at room temperature for 2.5 hr. The reaction mixture was neutralized with 1 N hydrochloric acid and extracted with ethyl acetate. The organic layer was washed with saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (15%-60% ethyl acetate/hexane) to give the title compound (330 mg, yield 83%) as a colorless oil.

Quelle