Reacción #8624

Ecuación de reacción

KHSO4

2-[5-benzyloxycarbonylamino-2-(2-nitro-benzenesulfonylamino)-pentanoylamino]-3-naphthalen-2-yl-propionic acid methyl ester

dibromoethane

potassium carbonate

→

desired product

2-[3-(3-Benzyloxycarbonylamino-propyl)-4-(2-nitro-benzene-sulfonyl)-2-oxo-piperazin-1-yl]-3-naphthalen-2-yl-propionic acid methyl ester

Disolventes

DMF

Condiciones de reacción

Tratamiento posterior

1. 1
   TemperaturaThe reaction mixture is cooled to room temperature
2. 2
   Extracciónthe resulting solution is extracted with ethyl acetate
3. 3
   OtroThe crude product is purified over silica (
4. 4
   Lavadosequential elution with EtOAc/hexanes mixtures 1:2, 1:1, 100% EtOAc

Procedimiento

A mixture of 2-[5-benzyloxycarbonylamino-2-(2-nitro-benzenesulfonylamino)-pentanoylamino]-3-naphthalen-2-yl-propionic acid methyl ester, 40, (2.4 g, 3.63 mmol), dibromoethane (3.8 mL, 4.36 mmol), potassium carbonate (5.0 g, 36.3 mmol) in DMF (50 mL) is stirred at 55° C. for 18 hours. The reaction mixture is cooled to room temperature, treated with 1M KHSO4 and the resulting solution is extracted with ethyl acetate. The crude product is purified over silica (sequential elution with EtOAc/hexanes mixtures 1:2, 1:1, 100% EtOAc, then EtOAc with 5% MeOH) to afford 2.76 g of the desired product.

Fuente