HCID 11487746, compound → HCID 11425688, compound

HRID 1007597Notes

Reaction equation

HRID 1007597 reaction equation
C([O:8][C@@:9]12[CH2:15][O:14][C@@H:13]1[C@H:12]([N:16]1[CH:24]=[C:22]([CH3:23])[C:20](=[O:21])[NH:19][C:17]1=[O:18])[O:11][C@@H:10]2[CH2:25][O:26]CC1C=CC=CC=1)C1C=CC=CC=1>C(O)C.[OH-].[Pd+2].[OH-]>[OH:8][C@@:9]12[CH2:15][O:14][C@@H:13]1[C@H:12]([N:16]1[CH:24]=[C:22]([CH3:23])[C:20](=[O:21])[NH:19][C:17]1=[O:18])[O:11][C@@H:10]2[CH2:25][OH:26]

Participants

4

Reactant 1

HCID 11487746HCID 11487746, compound

Product 1

HCID 11425688HCID 11425688, compound

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 702EthanolSolvent

Procedure

To a stirred solution of nucleoside 28 (180 mg, 0.40 mmol) in ethanol (3 cm3) was added 10% palladium hydroxide over carbon (90 mg). The mixture was degassed several times with argon and placed under a hydrogen atmosphere. The reaction mixture was stirred at room temperature for 6 h, then filtered through celite. The filtrate was evaporated under reduced pressure and the residue was purified by silica gel column chromatography using dichloromethane/methanol (96:4, v/v) as eluent to give nucleoside 29 as a white solid material (92 mg, 86%). δH (CD3OD) 7.79 (1H, d, J 1.2, 6-H), 5.91 (1H, d, J 2.5, 1′-H), 4.96 (1H, d, J 2.5, 2′-H), 4.92 (1H, d, J 7.4, 1″-Ha), 4.58 (1H, dd, J 0.9, 7.4, 1″-Hb), 3.98 (1H, dd, J 7.3, 12.8, 5′-Ha), 3.87-3.82 (2H, m, 4′-H, 5′-H(b), 3.34 (2H, s, 3′-OH, 5′-OH), 1.87 (3H, d, J 1.3, CH3). δC (CD3OD) 166.5 (C-4), 152.1 (C-2), 140.1 (C-6), 110.1 (C-5), 91.2 (C-2′), 85.1 (C-1′), 84.0 (C-4′), 79.6 (C-3′), 78.6 (C-1″), 61.1 (C-5′), 12.3 (CH3).

Workup

  1. customThe mixture was degassed several times with argon
  2. filtrationfiltered through celite
  3. customThe filtrate was evaporated under reduced pressure
  4. customthe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-b0178c847c2644719374be3e1dc19a34
Source dataset
uspto-grants-2004_09
Patent number
US06794499B2

Reaction notes

Loading…