5-Nitro-1-(2,3,5-tri-O-benzoyl-β-D-ribofuranosyl)-2(1H)-pyridinone → 5-Nitro-1-beta-D-ribofuranosylpyridin-2(1H)-one

HRID 419783Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 419783
[N+:1]([C:4]1[CH:5]=[CH:6][C:7](=[O:43])[N:8]([C@@H:10]2[O:32][C@H:31]([CH2:33][O:34]C(=O)C3C=CC=CC=3)[C@@H:21]([O:22]C(=O)C3C=CC=CC=3)[C@H:11]2[O:12]C(=O)C2C=CC=CC=2)[CH:9]=1)([O-:3])=[O:2]>N>[C@@H:10]1([N:8]2[CH:9]=[C:4]([N+:1]([O-:3])=[O:2])[CH:5]=[CH:6][C:7]2=[O:43])[O:32][C@H:31]([CH2:33][OH:34])[C@@H:21]([OH:22])[C@H:11]1[OH:12]

Komponenten

3

Edukt 1

HCID 112732675-Nitro-1-(2,3,5-tri-O-benzoyl-β-D-ribofuranosyl)-2(1H)-pyridinone

Produkt 1

HCID 666496085-Nitro-1-beta-D-ribofuranosylpyridin-2(1H)-one

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 222AmmoniaLösungsmittel

Versuchsvorschrift

A mixture of 5-nitro-1-(2′,3′,5′-tri-O-benzoyl-β-ribofuranosyl)-2-pyridone (10, R=Bz, Y=H, Z=CH; 100 mg, 0.17 mmol) and saturated methanolic ammonia (10 mL) was stirred at room temperature for 12 h. The mixture was concentrated to dryness, and the residue triturated with EtOH to precipitate 10 (R=Y=H, Z=CH), which was collected and recrystallized from water (37 mg, 81%) as a white solid. 1H NMR (DMSO-d6+D2O) δ 3.64 (m, 1H), 3.90 (m, 1H), 4.01 (m, 3H), 5.89 (s, 1H), 6.48 (d, J=10.4 Hz, 1H), 8.12 (dd, J=3.2, 10 Hz, 1H), 9.65 (d, J=3.2 Hz, 1H).

Aufarbeitung

  1. concentrationThe mixture was concentrated to dryness
  2. customthe residue triturated with EtOH
  3. customto precipitate 10 (R=Y=H, Z=CH), which
  4. customwas collected
  5. customrecrystallized from water (37 mg, 81%) as a white solid

Quellen und Nachweise

ORD-Eintrag
ord-e0e00f1c933d466e893aa2689309f616
Quelldatensatz
uspto-grants-2012_01
Patentnummer
US08093380B2

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