反応 #164193

反応方程式

(4-fluoro-phenyl)-(3-fluoro-phenylamino)-acetic acid

(R)-quinuclidin-3-ol

HOBT

DCC

→

title compound

収率 50.0%

(4-fluoro-phenyl)-(3-fluoro-phenylamino)-acetic acid (R)-(1-aza-bicyclo[2.2.2]oct-3-yl)ester

収率 50.0%

溶媒

THF

反応条件

後処理

1. 1
   その他The solvent is evaporated
2. 2
   workup.DISSOLUTIONthe crude is dissolved in EtOAc
3. 3
   ろ過the insoluble is filtered off
4. 4
   洗浄The clear solution is washed with 1N K2CO3
5. 5
   乾燥The organic layer is dried over Na2SO4
6. 6
   ろ過filtered
7. 7
   その他evaporated
8. 8
   その他The crude is purified by silica gel chromatography (EtOAc/MeOH=8/2)

実験手順

A mixture of (4-fluoro-phenyl)-(3-fluoro-phenylamino)-acetic acid (I83) (510 mg, 1.94 mmol), (R)-quinuclidin-3-ol (246 mg, 1.94 mmol), HOBT (356 mg, 2.32 mmol) and DCC (480 mg, 2.32 mmol) in THF (10 mL) is stirred at RT overnight (UPLC-MS monitoring: complete conversion). The solvent is evaporated, the crude is dissolved in EtOAc and the insoluble is filtered off. The clear solution is washed with 1N K2CO3 and then with brine. The organic layer is dried over Na2SO4, filtered and evaporated. The crude is purified by silica gel chromatography (EtOAc/MeOH=8/2) to give the title compound as a yellow oil (360 mg, 50% yield, mixture of diastereoisomers).

出典