반응 #164193

반응 방정식

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

(R)-quinuclidin-3-ol

HOBT

DCC

→

title compound

수율 50.0%

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

수율 50.0%

용매

THF

반응 조건

후처리

1. 1
   기타The solvent is evaporated
2. 2
   workup.DISSOLUTIONthe crude is dissolved in EtOAc
3. 3
   여과the insoluble is filtered off
4. 4
   세척The clear solution is washed with 1N K2CO3
5. 5
   건조The organic layer is dried over Na2SO4
6. 6
   여과filtered
7. 7
   기타evaporated
8. 8
   기타The crude is purified by silica gel chromatography (EtOAc/MeOH=8/2)

실험 절차

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).

출처