反应 #1881004

反应方程式

3-{4-[6-(1-Hydroxymethyl-propylamino)-2-oxo-3-propyl-3,7-dihydro-2H-purin-8-yl]-bicyclo[2.2.2]oct-1-yl}-propionic acid methyl ester

→

titled compound

3-[4-(7-Ethyl-5-oxo4-propyl-4,5,6,7-tetrahydro-1H-1,3,4,5a,8-pentaaza-as-indacen-2-yl)-bicyclo[2.2.2]oct-1-yl]-propionic acid

溶剂

SOCl2

反应条件

后处理

1. 1
   温度under reflux for 15 min
2. 2
   浓缩concentrated under reduced pressure
3. 3
   workup.DISSOLUTIONThe resulting residue was dissolved in a solution
4. 4
   workup.ADDITIONcontaining 1 mL of water, 0.5 mL of MeOH, and 0.1 mL of 10% aq. NaOH
5. 5
   workup.STIRRINGThe reaction mixture was stirred at rt for 30 min
6. 6
   workup.ADDITIONwith dilute 1 N HCl
7. 7
   浓缩concentrated
8. 8
   其他The resulting crude product was purified by preparative HPLC

实验过程

3-{4-[6-(1-Hydroxymethyl-propylamino)-2-oxo-3-propyl-3,7-dihydro-2H-purin-8-yl]-bicyclo[2.2.2]oct-1-yl}-propionic acid methyl ester (30 mg) was dissolved in 1 mL of SOCl2 and stirred under reflux for 15 min. The reaction mixture was then cooled to rt and concentrated under reduced pressure. The resulting residue was dissolved in a solution containing 1 mL of water, 0.5 mL of MeOH, and 0.1 mL of 10% aq. NaOH. The reaction mixture was stirred at rt for 30 min. It was then acidified to pH 2 with dilute 1 N HCl and concentrated. The resulting crude product was purified by preparative HPLC to afford the titled compound.

来源