Reacción #40291

Ecuación de reacción

1-(4-Hydroxy-phenyl)-pyrrole-2,5-dione

3-(4,5-dimethoxy-2-nitro-benzyloxycarbonylamino)-butyric acid

DIC

→

3-(4,5-dimethoxy-2-nitro benzyloxycarbonyl-amino)-butyric acid 4-(2,5-dioxo-2,5-dihydro-pyrrol-1-yl)-phenyl ester

Disolventes

THF

Condiciones de reacción

Tratamiento posterior

1. 1
   OtroThe cooling bath is removed after 1 hour
2. 2
   workup.WAITthe reaction mixture is left at room temperature o/n
3. 3
   OtroThe solvent is evaporated in vacuo

Procedimiento

1-(4-Hydroxy-phenyl)-pyrrole-2,5-dione (1 mmol), NHS (1.0 mmol) and 3-(4,5-dimethoxy-2-nitro-benzyloxycarbonylamino)-butyric acid (1 mmol) is dissolved in THF (3 mL). The solution is cooled to 0° C. and treated dropwise with DIC (1.2 mmol). The cooling bath is removed after 1 hour and the reaction mixture is left at room temperature o/n. The solvent is evaporated in vacuo and the pure product (3-(4,5-dimethoxy-2-nitro benzyloxycarbonyl-amino)-butyric acid 4-(2,5-dioxo-2,5-dihydro-pyrrol-1-yl)-phenyl ester) is isolated by silica column purification using EtOAc-heptane (1:4 then 1:2 then 1:1) as eluent.

Fuente