Reacción #668012

Ecuación de reacción

L-glutamic acid 1,5-dibenzyl ester p-toluenesulfonate

Boc-Ser

WSC

HOBt

→

N-tert-butoxycarbonyl-L-seryl-L-glutamic acid 1,5-dibenzyl ester

Rendimiento 94.3%

Disolventes

ethyl acetate

DMF

Condiciones de reacción

Tratamiento posterior

1. 1
   Temperaturacooling
2. 2
   LavadoThe mixture is washed successively with 1N hydrochloric acid
3. 3
   Secadoa saturated aqueous sodium hydrogen carbonate solution, and a saturated aqueous sodium chloride solution, dried
4. 4
   Concentraciónconcentrated under reduced pressure
5. 5
   FiltraciónThe precipitated solid is collected by filtration
6. 6
   Lavadowashed with ether

Procedimiento

To a solution of L-glutamic acid 1,5-dibenzyl ester p-toluenesulfonate (10.0 g), Boc-Ser (4.1 g) and TEA (2.0 g) in DMF (200 ml) are added with stirring WSC (5.0 g) and HOBt (4.0 g) under ice-cooling. The mixture is stirred at room temperature for 20 hours, and thereto is added ethyl acetate (200 ml). The mixture is washed successively with 1N hydrochloric acid, a saturated aqueous sodium hydrogen carbonate solution, and a saturated aqueous sodium chloride solution, dried, and concentrated under reduced pressure. The precipitated solid is collected by filtration, and washed with ether to give N-tert-butoxycarbonyl-L-seryl-L-glutamic acid 1,5-dibenzyl ester (9.7 g) as colorless crystals.

Fuente