Reaction #1797513

Reaction equation

adefovir

3-hexadecyloxy-1-propanol

DCC

→

hexadecyloxypropyl-adefovir

Solvents

pyridine

Conditions

Workup

1. 1
   TemperatureThe mixture was heated
2. 2
   Temperatureto reflux
3. 3
   Temperaturethen cooled
4. 4
   Filtrationfiltered
5. 5
   ConcentrationThe filtrate was concentrated under reduced pressure
6. 6
   WashElution of the column with 9:1 dichloromethane/methanol

Procedure

To a mixture of adefovir (1.36 g, 5 mmol) and 3-hexadecyloxy-1-propanol (1.8 g, 6 mmol) in dry pyridine was added DCC (2.06 g, 10 mmol). The mixture was heated to reflux and stirred 18 h then cooled and filtered. The filtrate was concentrated under reduced pressure and the residue was applied to a short column of silica gel. Elution of the column with 9:1 dichloromethane/methanol yielded hexadecyloxypropyl-adefovir (HDP-ADV) as a white powder.

Source