Réaction #1797513

ord-3281dd10aeb244d2b93fd18161c418c9

Équation de réaction

Nc1ncnc2c1ncn2CCOCP(=O)(O)O
adefovir
CCCCCCCCCCCCCCCCOCCCO
3-hexadecyloxy-1-propanol
C(=NC1CCCCC1)=NC1CCCCC1
DCC
CCCCCCCCCCCCCCCCOCCCOP(=O)(O)COCCn1cnc2c(N)ncnc21
hexadecyloxypropyl-adefovir

Solvants

Conditions de réaction

Conditions détaillées
See reaction.notes.procedure_details.

Traitement

  1. 1
    TempératureThe mixture was heated
  2. 2
    Températureto reflux
  3. 3
    Températurethen cooled
  4. 4
    Filtrationfiltered
  5. 5
    ConcentrationThe filtrate was concentrated under reduced pressure
  6. 6
    LavageElution of the column with 9:1 dichloromethane/methanol

Mode opératoire

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

DOI: 10.6084/m9.figshare.5104873.v1Brevet: US07790703B2uspto-grants-2010_09