反应 #164193

反应方程式

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

(R)-quinuclidin-3-ol

HOBT

DCC

→

title compound

收率 50.0%

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

收率 50.0%

溶剂

THF

反应条件

后处理

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

实验过程

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).

来源