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 419783노트

반응식

HRID 419783 반응식
[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]

참가 물질

3

반응물 1

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

생성물 1

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

시약·촉매·용매 1

HCID 222Ammonia용매

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-e0e00f1c933d466e893aa2689309f616
출처 데이터셋
uspto-grants-2012_01
특허 번호
US08093380B2

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