反应 #417019

反应方程式

Nα,Nε -di-benzyloxycarbonyllysine

diethylphosphoryl cyanide

5'-O-(N-alanylisoleucyl)-5-fluorouridine hydrochloride

triethylamine

→

5'-O-[N-{N-(Nα,Nε -di benzyloxycarbonyllysyl)alanyl}isoleucyl]-5-fluorouridine

收率 45.9%

溶剂

dimethylformamide

dimethylformamide

反应条件

后处理

1. 1
   workup.ADDITIONTo this solution was added under ice-
2. 2
   workup.WAITto stand overnight at room temperature
3. 3
   浓缩concentrated under reduced pressure
4. 4
   其他The residue was subjected to separation/purification by way of silica gel column chromatography (5×20 cm

实验过程

0.46 Gram of 5'-O-(N-alanylisoleucyl)-5-fluorouridine hydrochloride obtained in Example 4 was dissolved in dimethylformamide (30 ml), and 1.42 g (3.42 mmol) of Nα,Nε -di-benzyloxycarbonyllysine and 0.90 g (5.52 mmol) of diethylphosphoryl cyanide were then added. To this solution was added under ice-cooling a solution of 1.30 g (12.9 mmol) of triethylamine in dimethylformamide, and the mixture was stirred for 1 hour at room temperature, allowed to stand overnight at room temperature and concentrated under reduced pressure. The residue was subjected to separation/purification by way of silica gel column chromatography (5×20 cm; a linear gradient of chloroform containing 3%→6% methanol) whereby 1.20 g (45.9%) of 5'-O-[N-{N-(Nα,Nε -di benzyloxycarbonyllysyl)alanyl}isoleucyl]-5-fluorouridine was obtained as a colorless powdery solid.

来源