Reacción #170706

Ecuación de reacción

WSC.HCl

1-phenyl-5-(3-propylphenyl)-1H-pyrazol-3-ylamine

(R)-2,3-bis-tert-butoxycarbonylaminopropionic acid

HOBt

→

titled compound

Rendimiento 91.5%

{(R)-2-tert-Butoxycarbonylamino-2-[1-phenyl-5-(3-propylphenyl)-1H-pyrazol-3-ylcarbamoyl]-ethyl}carbamic acid tert-butyl ester

Rendimiento 91.5%

Disolventes

H2O

water

DMF

Condiciones de reacción

Tratamiento posterior

1. 1
   Extraccióna saturated aqueous solution of sodium hydrogen carbonate, and the mixture was extracted with ethyl acetate
2. 2
   LavadoThe separated organic layer was washed with a saturated aqueous solution of sodium chloride
3. 3
   Secadodried over anhydrous sodium sulfate
4. 4
   Concentraciónconcentrated under reduced pressure
5. 5
   OtroThe resulting residue was purified by silica gel column chromatography (eluent: n-hexane/ethyl acetate=2/1)

Procedimiento

To a solution of 1-phenyl-5-(3-propylphenyl)-1H-pyrazol-3-ylamine (177 mg) prepared according to the same procedures as Preparation 8 in DMF (1.8 ml) were added (R)-2,3-bis-tert-butoxycarbonylaminopropionic acid (292 mg), HOBt.H2O (147 mg) and WSC.HCl (184 mg), and the mixture was stirred at room temperature for 2 hours. To this reaction solution were added water and a saturated aqueous solution of sodium hydrogen carbonate, and the mixture was extracted with ethyl acetate. The separated organic layer was washed with a saturated aqueous solution of sodium chloride, dried over anhydrous sodium sulfate, and then concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography (eluent: n-hexane/ethyl acetate=2/1) to give the titled compound (329 mg).

Fuente