Reaktion #1479009

ord-3c9c3d7cc64244439ca2d5a8e5877c56

Reaktionsgleichung

N
ammonia
CC(=O)OC[C@@]1(C#N)O[C@@H](n2cnc3c(N)nc(F)nc32)C[C@@H]1OC(C)=O
Compound 7
CC(=O)OC[C@@]1(C#N)O[C@@H](n2cnc3c(N)nc(F)nc32)C[C@@H]1OC(C)=O
3′, 5′-di-O-acetyl-4′-C-cyano-2′-deoxy-2-fluoroadenosine
N#C[C@]1(CO)O[C@@H](n2cnc3c(N)nc(F)nc32)C[C@@H]1O
4′-C-cyano-2′-deoxy-2-fluoroadenosine

Lösungsmittel

Reaktionsbedingungen

Detaillierte Bedingungen
See reaction.notes.procedure_details.

Aufarbeitung

  1. 1
    SonstigeThe resultant reaction mixture
  2. 2
    Einengenwas concentrated under reduced pressure
  3. 3
    Sonstigethe resultant residue was purified by means of silica gel column chromatography (silica gel 10 ml, hexane/ethyl acetate (5:1), ethyl acetate, ethyl acetate/methanol (10:1))

Vorschrift

Compound 7 (53.7 mg, 0.142 mmol) was dissolved in methanol (1.90 ml), and 28% aqueous ammonia (1.30 ml) was added to the resultant solution, followed by stirring at room temperature for 30 minutes. The resultant reaction mixture was concentrated under reduced pressure, and then the resultant residue was purified by means of silica gel column chromatography (silica gel 10 ml, hexane/ethyl acetate (5:1), ethyl acetate, ethyl acetate/methanol (10:1)), to thereby yield compound 8 (30.2 mg, 0.10 mmol, 72.3%).

Quelle

DOI: 10.6084/m9.figshare.5104873.v1Patent: US07339053B2uspto-grants-2008_03