반응 #164230

반응 방정식

4-methyl-phenyl-amino-phenyl-acetic acid

DCC

HOBt

3(R)-quinuclidinol

→

title compound

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

용매

THF

반응 조건

후처리

1. 1
   기타The solvent is evaporated
2. 2
   건조The organic phase is dried over Na2SO4
3. 3
   여과filtered
4. 4
   기타evaporated to dryness
5. 5
   workup.DISSOLUTIONThe resulting crude is dissolved in little DCM
6. 6
   여과filtered
7. 7
   기타to remove the insoluble
8. 8
   농축The solution is concentrated under vacuum

실험 절차

To a solution of 4-methyl-phenyl-amino-phenyl-acetic acid (I244) (870 mg, 3.60 mmol) in dry THF (35 mL), are added DCC (891 mg, 4.32 mmol), HOBt (583 mg, 4.32 mmol) and 3(R)-quinuclidinol (915 mg, 7.20 mmol). The resulting mixture is stirred at RT for 48 hours (UPLC-MS monitoring: complete conversion). The solvent is evaporated and the residue is portioned between EtOAc and 1M K2CO3. The organic phase is dried over Na2SO4, filtered and evaporated to dryness. The resulting crude is dissolved in little DCM and filtered to remove the insoluble. The solution is concentrated under vacuum to obtain the title compound as a yellow solid, which is used in the next step without any further purification.

출처