Reaktion #44394

Reaktionsgleichung

product

5′-chloro-N-(1-ethylpropyl)-3-fluoro-2′-hydroxy-[1,1′-biphenyl]-4-carboxamide

product

(2R)-2-(4-methylphenoxy)-propanoic acid, methyl ester

potassium carbonate

→

title compound

(2S)-2-[[5-chloro-4′-[[(1-ethylpropyl)amino]carbonyl]-3′-fluoro[1,1′-biphenyl]-2-yl]oxy]-propanoic acid

Lösungsmittel

acetonitrile

water

Reaktionsbedingungen

Aufarbeitung

1. 1
   TemperaturThe reaction mixture was cooled
2. 2
   Extraktionextracted with diethyl ether (3×10 ml)
3. 3
   WaschenThe organic fractions were washed with brine
4. 4
   Trocknendried (MgSO4)
5. 5
   Einengenconcentrated in vacuo
6. 6
   workup.DISSOLUTIONThe resulting yellow oil was dissolved in a 1:1 mixture of THF/methanol (10 ml) and 1M NaOH
7. 7
   workup.ADDITIONadded (1.1 ml)
8. 8
   workup.STIRRINGThe mixture was stirred at room temperature for 4 h
9. 9
   Einengenconcentrated in vacuo
10. 10
    SonstigeThe residue was purified by RPHPLC

Vorschrift

The product of step c) (300 mg), the product of step d) (219 mg) and potassium carbonate (135 mg) in acetonitrile (10 ml) were charged to a flask and stirred at 50° C. for 16 h. The reaction mixture was cooled, diluted with water (20 ml) and extracted with diethyl ether (3×10 ml). The organic fractions were washed with brine, dried (MgSO4) and concentrated in vacuo. The resulting yellow oil was dissolved in a 1:1 mixture of THF/methanol (10 ml) and 1M NaOH added (1.1 ml). The mixture was stirred at room temperature for 4 h and then concentrated in vacuo. The residue was purified by RPHPLC to give the title compound as a white solid (175 mg).

Quelle