Reacción #58048

Ecuación de reacción

Ethanol

2-butyl-3-ethoxycarbonyl-succinic acid diethyl ester

NaH

(5-Bromomethyl-pyridin-2-yl)-carbamic acid tert-butyl ester

→

2-(6-tert-butoxycarbonylamino-pyridin-3-ylmethyl)-3-butyl-2-ethoxycarbonyl-succinic acid diethyl ester

Rendimiento 78.6%

Disolventes

DMF

H2O

Condiciones de reacción

Tratamiento posterior

1. 1
   Extracciónextracted with ethyl acetate
2. 2
   LavadoThe organic layer was washed with water
3. 3
   Concentraciónconcentrated under reduced pressure
4. 4
   OtroThe product was purified by column chromatography (heptane/ethyl acetate, 4:1 to 1:1)

Procedimiento

A solution of 2-butyl-3-ethoxycarbonyl-succinic acid diethyl ester (1 g, 3 mmol) and NaH (119 mg, 5 mmol) in DMF (20 ml) was stirred for 60 minutes at 0° C. under argon. (5-Bromomethyl-pyridin-2-yl)-carbamic acid tert-butyl ester (1.425 g, 5 mmol) was added and the mixture was stirred at room temperature for one week. Ethanol (1 ml) was added and the reaction was poured into H2O and extracted with ethyl acetate. The organic layer was washed with water and concentrated under reduced pressure. The product was purified by column chromatography (heptane/ethyl acetate, 4:1 to 1:1) to give 2-(6-tert-butoxycarbonylamino-pyridin-3-ylmethyl)-3-butyl-2-ethoxycarbonyl-succinic acid diethyl ester (1.2 g, 71.3%).

Fuente