Sodium Hydroxide → HCID 178520964, compound

HRID 1160664Notes

Reaction equation

HRID 1160664 reaction equation
C([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]CC4C=CC=CC=4)[CH2:16][CH2:15]3)[CH:12]=[N:11][C:10]=2[C:9]1=[O:31])C1C=CC=CC=1.[OH-].[Na+].[H][H]>[OH-].[Pd+2].[OH-].[C].CN(C)C=O>[C@@H:14]1([N:13]2[C:28]3[N:29]=[CH:30][N:8]=[C:9]([OH:31])[C:10]=3[N:11]=[CH:12]2)[O:27][C@H:17]([CH2:18][OH:19])[CH2:16][CH2:15]1

Participants

6

Reactant 3

HCID 14798Sodium HydroxideHCID 11647353N1,5'-O-dibenzyl-2',3'-dideoxyinosineHCID 178418361HCID 178418361, compound

Product 1

HCID 178520964HCID 178520964, compoundYield 71.1%

Reagents, catalysts & solvents 2

HCID 178502593HCID 178502593, compoundCatalystHCID 6228DimethylformamideSolvent

Procedure

To a N,N-dimethylformamide solution (1 mL) of N1,5′-O-dibenzyl-2′,3′-dideoxyinosine (52 mg, 0.125 mmol), an aqueous solution of sodium hydroxide (0.3 mL) at a concentration of 1 mol/L was added, and the mixture was stirred at room temperature for 2 hours. To the obtained solution, 20% palladium hydroxide-carbon (10 mg) was added, and the mixture was stirred at room temperature for 2 hours in an atmosphere of hydrogen (1 atm) and thereafter stirred at 80° C. for 16 hours and at 100° C. for 6 hours. 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 10 g of silica gel and a mixed solvent of dichloromethane and methanol (4:1) as an eluting solution), 21 mg of the intended product was obtained in a yield of 70% as a white solid.

Workup

  1. stirringstirred at 80° C. for 16 hours and at 100° C. for 6 hours
  2. customThe palladium catalyst was removed from the obtained reaction mixture by filtration
  3. concentrationthe resultant filtrate was concentrated under reduced pressure
  4. customAfter purification by chromatography (

Sources & evidence

ORD record
ord-c2dd916b43d04c129afe42deb089fa9d
Source dataset
uspto-grants-2010_10
Patent number
US07816513B2

Reaction notes

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