تفاعل #8624

معادلة التفاعل

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

المذيبات

DMF

ظروف التفاعل

المعالجة

1. 1
   درجة الحرارةThe reaction mixture is cooled to room temperature
2. 2
   استخلاصthe resulting solution is extracted with ethyl acetate
3. 3
   أخرىThe crude product is purified over silica (
4. 4
   غسيلsequential elution with EtOAc/hexanes mixtures 1:2, 1:1, 100% EtOAc

الإجراء التجريبي

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.

المصدر