HCID 53686061, compound → HCID 53936772, compound

HRID 232386Notes

Reaction equation

HRID 232386 reaction equation
C([O:8][C:9]1[CH:14]=[C:13]([CH3:15])[C:12]([CH2:16][C:17]([NH:19][CH2:20][C@H:21]2[O:25][C@@H:24]([N:26]3[CH:33]=[C:32]([CH2:34][CH3:35])[C:30](=[O:31])[NH:29][C:27]3=[O:28])[CH2:23][C@@H:22]2[OH:36])=[O:18])=[C:11]([CH3:37])[CH:10]=1)C1C=CC=CC=1>CO.[Pd]>[CH2:34]([C:32]1[C:30](=[O:31])[NH:29][C:27](=[O:28])[N:26]([CH:33]=1)[C@@H:24]1[O:25][C@H:21]([CH2:20][NH:19][C:17](=[O:18])[CH2:16][C:12]2[C:13]([CH3:15])=[CH:14][C:9]([OH:8])=[CH:10][C:11]=2[CH3:37])[C@@H:22]([OH:36])[CH2:23]1)[CH3:35]

Participants

4

Reactant 1

HCID 53686061HCID 53686061, compound

Product 1

HCID 53936772HCID 53936772, compoundYield 76%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

24 mg of 5'-[2-(4-benzyloxy-2,6-dimethylphenyl)acetamido]-2',5'-dideoxy-5-ethyluridine were dissolved in 50 ml of methanol and the solution was hydrogenated over 15 mg of 5% palladium-on-charcoal catalyst at room temperature and under atmospheric pressure for 72 hours. The catalyst was removed by filtration and the filtrate was evaporated to give 15 mg of 2',5'-dideoxy-5-ethyl-5'-[2-(4-hydroxy-2,6-dimethylphenyl)acetamido]uridine of melting point 221°-225° C. (decomposition).

Workup

  1. customThe catalyst was removed by filtration
  2. customthe filtrate was evaporated

Sources & evidence

ORD record
ord-f1da0ec9978e4eab9ada9611ac66c3f0
Source dataset
uspto-grants-1989_07
Patent number
US04851519

Reaction notes

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