Chloride → 3′-Azido-3′-deoxyadenosine

HRID 1486232Notes

Reaction equation

HRID 1486232 reaction equation
[N:1]([C@@H:4]1[C@@H:8]([CH2:9][OH:10])[O:7][C@@H:6]([N:11]2[C:21]3[N:20]=[C:18](N)[NH:17][C:15](=O)[C:14]=3[N:13]=[CH:12]2)[C@@H:5]1[OH:22])=[N+:2]=[N-:3].[Cl-].[C:24](Cl)(=[O:31])[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1.[OH-].[NH4+:34]>N1C=CC=CC=1.O>[N:1]([C@@H:4]1[C@@H:8]([CH2:9][OH:10])[O:7][C@@H:6]([N:11]2[C:21]3[N:20]=[CH:18][N:17]=[C:15]([NH2:34])[C:14]=3[N:13]=[CH:12]2)[C@@H:5]1[OH:22])=[N+:2]=[N-:3].[N:1]([C@@H:4]1[C@@H:8]([CH2:9][OH:10])[O:7][C@@H:6]([N:11]2[C:21]3[N:20]=[CH:18][N:17]=[C:15]([NH:34][C:24](=[O:31])[C:25]4[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=4)[C:14]=3[N:13]=[CH:12]2)[C@@H:5]1[OH:22])=[N+:2]=[N-:3]

Participants

8

Reactant 4

HCID 312ChlorideHCID 7412Benzoyl chlorideHCID 14923Ammonium HydroxideHCID 1354384763'-AZIDO-3'-DEOXYGUANOSINE

Product 2

HCID 52730123′-Azido-3′-deoxyadenosineHCID 86729963HCID 86729963, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 1049PyridineSolvent

Procedure

3′-Azido-3′-deoxyadenosine is synthesized as described by Robins et al. (J. Org. Chem. 66:8204-8210, 2001). 3′-azido-3′-deoxyguanosine (2.92 g; 10 mmol) is dissolved in anhydrous pyridine (60 mL) with vigorous stirring under an argon atmosphere and cooled on an ice bath, followed by treatment with trimethylsylil chloride (3 molar equivalents; mol eq), and stirring for 60 minutes at room temperature. The resulting solution containing the sylilated nucleoside is cooled on an ice bath and treated with benzoyl chloride (1.2 mol eq), allowed to reach room temperature, and then stirred for 4 hours. Water (10 mL) is added and the solution is stirred for 10 minutes. Concentrated ammonium hydroxide (20 mL) is added and the reaction mixture is stirred for 15 minutes at room temperature. The resulting mixture was then evaporated to dryness under reduced pressure. The dried residue is stirred with cold water, filtered, and dried under high vacuum with phosphorus pentoxide, yielding 3′-azido-6-N-benzoyl 3′-deoxyadenosine.

Workup

  1. temperaturecooled on an ice bath
  2. stirringstirring for 60 minutes at room temperature
  3. temperatureis cooled on an ice bath
  4. customto reach room temperature
  5. stirringstirred for 4 hours
  6. stirringthe solution is stirred for 10 minutes
  7. stirringthe reaction mixture is stirred for 15 minutes at room temperature
  8. customThe resulting mixture was then evaporated to dryness under reduced pressure
  9. stirringThe dried residue is stirred with cold water
  10. filtrationfiltered
  11. dry with materialdried under high vacuum with phosphorus pentoxide

Sources & evidence

ORD record
ord-988da8596a0844f7aead8ff3c929bc1f
Source dataset
uspto-grants-2016_08
Patent number
US09422550B2

Reaction notes

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