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

HRID 2065524Notes

Reaction equation

HRID 2065524 reaction equation
[CH2:1]([N:8]1[CH:40]=[N:39][C:38]2[N:13]([C@@H:14]3[O:37][C@H:27]([CH2:28][O:29][CH2:30][C:31]4[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=4)[C@@H:21](OC(SC)=S)[C@H:15]3OC(SC)=S)[CH:12]=[N:11][C:10]=2[C:9]1=[O:41])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[PH2](O)=O.C(N1CCCCC1)C.N(C(C)(C)C#N)=NC(C)(C)C#N>C(#N)C>[CH2:1]([N:8]1[CH:40]=[N:39][C:38]2[N:13]([C@@H:14]3[O:37][C@H:27]([CH2:28][O:29][CH2:30][C:31]4[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=4)[CH:21]=[CH:15]3)[CH:12]=[N:11][C:10]=2[C:9]1=[O:41])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 6547AzobisisobutyronitrileHCID 11527429n1,5'-o-Dibenzyl-2',3'-bis-o-[(methylthio)thiocarbonyl]inosineHCID 178462538HCID 178462538, compound

Product 1

HCID 11683075N1,5'-O-dibenzyl-2',3'-didehydro-2',3'-dideoxyinosineYield 72.4%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent2×

Conditions

Temperature
90 °C

Procedure

An acetonitrile solution (1 mL) of N1,5′-O-dibenzyl-2′,3′-bis-O-[(methylthio)thiocarbonyl]inosine (314 mg, 0.5 mmol) was heated to 80° C. To this solution, an acetonitrile solution (1 mL) of N-ethylpiperidine hypophosphite (358 mg, 2 mmol) and 2,2′-azobisisobutyronitrile (16.4 mg, 0.1 mmol) were added, and the mixture was then stirred at 90° C. for one hour. After the reaction mixture was cooled, the reaction was terminated with the addition of water (3 mL). The reaction mixture was extracted by the addition of ethyl acetate (15 mL), and the resultant organic layer was dried over anhydrous magnesium sulfate and concentrated under reduced pressure. After purification by chromatography (using 12 g of silica gel and a mixed solvent of hexane and ethyl acetate (1:2) as an eluting solution), 150 mg of the intended product was obtained in a yield of 71% as a colorless oily material.

Workup

  1. temperatureAfter the reaction mixture was cooled
  2. customthe reaction was terminated with the addition of water (3 mL)
  3. extractionThe reaction mixture was extracted by the addition of ethyl acetate (15 mL)
  4. dry with materialthe resultant organic layer was dried over anhydrous magnesium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customAfter purification by chromatography (

Sources & evidence

ORD record
ord-7f7648a00db640009201159166462a81
Source dataset
uspto-grants-2012_10
Patent number
US08288526B2

Reaction notes

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