N1,5'-O-dibenzyl-2',3'-didehydro-2',3'-dideoxyinosine → N1,5'-O-dibenzyl-2',3'-dideoxyinosine

HRID 2065525Notes

Reaction equation

HRID 2065525 reaction equation
[CH2:1]([N:8]1[CH:30]=[N:29][C:28]2[N:13]([C@@H:14]3[O:27][C@H:17]([CH2:18][O:19][CH2:20][C:21]4[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=4)[CH:16]=[CH:15]3)[CH:12]=[N:11][C:10]=2[C:9]1=[O:31])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H][H]>[C].[Pd].CO>[CH2:1]([N:8]1[CH:30]=[N:29][C:28]2[N:13]([C@@H:14]3[O:27][C@H:17]([CH2:18][O:19][CH2:20][C:21]4[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=4)[CH2:16][CH2:15]3)[CH:12]=[N:11][C:10]=2[C:9]1=[O:31])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 2

HCID 11683075N1,5'-O-dibenzyl-2',3'-didehydro-2',3'-dideoxyinosineHCID 178418361HCID 178418361, compound

Product 1

HCID 11647353N1,5'-O-dibenzyl-2',3'-dideoxyinosineYield 90%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 887MethanolSolvent

Procedure

To a methanol solution (1 mL) of N1,5′-O-dibenzyl-2′,3′-didehydro-2′,3′-dideoxyinosine (207 mg, 0.5 mmol), 5% palladium-carbon (20 mg) was added, and the mixture was stirred at room temperature for 2 hours in an atmosphere of hydrogen (1 atm). The palladium catalyst was removed from the obtained reaction mixture by filtration, and the resultant filtrate was concentrated under reduced pressure. After purification by chromatography (using 15 g of silica gel and ethyl acetate as an eluting solution), 187 mg of the intended product was obtained in a yield of 90% as a white solid.

Workup

  1. customThe palladium catalyst was removed from the obtained reaction mixture by filtration
  2. concentrationthe resultant filtrate was concentrated under reduced pressure
  3. customAfter purification by chromatography (
  4. customwas obtained in a yield of 90% as a white solid

Sources & evidence

ORD record
ord-1bd7916cacdc43a584b7535aa95dcd76
Source dataset
uspto-grants-2012_10
Patent number
US08288526B2

Reaction notes

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