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 419783ノート

反応式

HRID 419783 の反応式
[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]

参加物

3

反応物 1

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 222Ammonia溶媒

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-e0e00f1c933d466e893aa2689309f616
出典データセット
uspto-grants-2012_01
特許番号
US08093380B2

反応ノート

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