HCID 136038657, compound → HCID 136015496, compound

HRID 990004Notes

Reaction equation

HRID 990004 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 chromatography. 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 chromatography

Sources & evidence

ORD record
ord-040ab2e6d92041d8bf64f6cc45f3d8a4
Source dataset
uspto-grants-2002_10
Patent number
US06458772B1

Reaction notes

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