反応 #44394

反応方程式

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

溶媒

acetonitrile

water

反応条件

後処理

1. 1
   温度The reaction mixture was cooled
2. 2
   抽出extracted with diethyl ether (3×10 ml)
3. 3
   洗浄The organic fractions were washed with brine
4. 4
   乾燥dried (MgSO4)
5. 5
   濃縮concentrated 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
   濃縮concentrated in vacuo
10. 10
    その他The residue was purified by RPHPLC

実験手順

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).

出典