HCID 136038657, compound → HCID 136015496, compound

HRID 1790831Notes

Reaction equation

HRID 1790831 reaction equation
[F:1][C@@H:2]1[C@@H:6]([CH2:7][O:8][C:9](=[O:34])[CH2:10][CH2:11][C:12]([O:14][CH:15]([CH2:25][O:26]CC2C=CC=CC=2)[CH2:16][O:17]CC2C=CC=CC=2)=[O:13])[O:5][C@@H:4]([N:35]2[C:45]3[N:44]=[C:42]([NH2:43])[NH:41][C:39](=[O:40])[C:38]=3[N:37]=[CH:36]2)[CH2:3]1>C(OCC)(=O)C.CO.C(O)(=O)C.[Pd]>[F:1][C@@H:2]1[C@@H:6]([CH2:7][O:8][C:9](=[O:34])[CH2:10][CH2:11][C:12]([O:14][CH:15]([CH2:16][OH:17])[CH2:25][OH:26])=[O:13])[O:5][C@@H:4]([N:35]2[C:45]3[N:44]=[C:42]([NH2:43])[NH:41][C:39](=[O:40])[C:38]=3[N:37]=[CH:36]2)[CH2:3]1

Participants

6

Reactant 1

HCID 136038657HCID 136038657, compound

Product 1

HCID 136015496HCID 136015496, compound

Reagents, catalysts & solvents 4

HCID 23938PalladiumCatalystHCID 176Acetic AcidSolventHCID 887MethanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of 2′,3′-dideoxy-3′-fluoro-5′-O-[3-(1,3-dibenzyloxy-2-propyloxy carbonyl)propanoyl]guanosine (3.2 g, 5.13 mmole) in 50 ml ethyl acetate, 50 ml methanol and 10 ml acetic acid was hydrogenated with palladium black (0.6 g) under 40 psi overnight. The catalyst was filtered and washed with methanol, The solution was evaporated under reduced pressure and the product was isolated by silica gel column chromathography. Yield: 1.64 g

Workup

  1. filtrationThe catalyst was filtered
  2. washwashed with methanol
  3. customThe solution was evaporated under reduced pressure
  4. customthe product was isolated by silica gel column chromathography

Sources & evidence

ORD record
ord-ee3cee96d5f64d1fada78751a9e03d51
Source dataset
uspto-grants-2006_07
Patent number
US07071173B2

Reaction notes

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