1-(2',3',5'-Tri-o-benzoyl-beta-l-ribofuranosyl)pyridine-4-one-3-carboxamide → 1-beta-l-Ribofuranosylpyridine-4-one-3-carboxamide

HRID 366949Notes

Reaction equation

HRID 366949 reaction equation
C([O:9][C@H:10]1[C@@H:14]([O:15]C(=O)C2C=CC=CC=2)[C@H:13]([CH2:24][O:25]C(=O)C2C=CC=CC=2)[O:12][C@@H:11]1[N:34]1[CH:39]=[CH:38][C:37](=[O:40])[C:36]([C:41]([NH2:43])=[O:42])=[CH:35]1)(=O)C1C=CC=CC=1>N>[C@H:11]1([N:34]2[CH:39]=[CH:38][C:37](=[O:40])[C:36]([C:41]([NH2:43])=[O:42])=[CH:35]2)[O:12][C@@H:13]([CH2:24][OH:25])[C@H:14]([OH:15])[C@@H:10]1[OH:9]

Participants

3

Reactant 1

HCID 120431211-(2',3',5'-Tri-o-benzoyl-beta-l-ribofuranosyl)pyridine-4-one-3-carboxamide

Product 1

HCID 219717661-beta-l-Ribofuranosylpyridine-4-one-3-carboxamideYield 99%

Reagents, catalysts & solvents 1

HCID 222AmmoniaSolvent

Procedure

Compound 33 (0.5 g, 0.86 mmol) was dissolved in dry methanolic ammonia (50 mL) and stirred for 15 h in a bomb at room temperature. The solution is then concentrated to a small volume and cooled overnight at 4° C. The crystalline product formed was filtered off, washed with cold methanol. The solid was recyrstallized from absolute ethanol to give 0.23 g (87%) of pure product: mp 209-211° C.; 1H NMR (Me2SO-d6) δ 3.60 (m, 2H, C5'H), 3.93 (m, 1H, C4'H), 4.09 (m, 1H, C3'H), 4.34 (m, 1H, C2'H), 5.11 (m, 1H, C5'OH, D2O exchangeable), 5.22 and 5.47 (2m, 2H, C2',3' OH, D2O exchangeable), 5.84 (d, 1H, J1',2' =6.3 Hz, C1'H), 7.21 (m, 2H, PhH), 7.64 (m, 2H, PhH and CONH2) and 8.44 (s, 1H, CONH2). Anal. Calc. for C11H14N2O6 (270.24): C, 48.89; H, 5.22; N,10.37. Found: C, 48.89; H, 5.42; N, 10.51.

Workup

  1. concentrationThe solution is then concentrated to a small volume
  2. temperaturecooled overnight at 4° C
  3. customThe crystalline product formed
  4. filtrationwas filtered off
  5. washwashed with cold methanol

Sources & evidence

ORD record
ord-640ee9dc2fce4729b08ee2d96ea6c928
Source dataset
uspto-grants-2000_10
Patent number
US06130326

Reaction notes

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