反応 #1951041

ord-621fd0a6367e4a27b776a93ec8441eaa

反応方程式

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

溶媒

反応条件

詳細条件
See reaction.notes.procedure_details.

後処理

  1. 1
    その他The resultant reaction mixture
  2. 2
    濃縮was concentrated under reduced pressure
  3. 3
    その他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))

実験手順

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%).

出典

DOI: 10.6084/m9.figshare.5104873.v1特許: US07625877B2uspto-grants-2009_12