Реакция #1951041

ord-621fd0a6367e4a27b776a93ec8441eaa

Уравнение реакции

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

Растворители

Условия реакции

Подробные условия
See reaction.notes.procedure_details.

Обработка

  1. 1
    ДругоеThe resultant reaction mixture
  2. 2
    Концентрированиеwas concentrated under reduced pressure
  3. 3
    Другоеthe 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))

Методика

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%).

Источник

DOI: 10.6084/m9.figshare.5104873.v1Патент: US07625877B2uspto-grants-2009_12