Acetic Acid → HCID 135476520, compound

HRID 366966Notes

Reaction equation

HRID 366966 reaction equation
[Na].[CH2:2]([OH:9])[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.Br[C:11]1[N:12]([C:21]2[N:22]=[C:23]([NH2:29])[NH:24][C:25](=[O:28])[C:26]=2[N:27]=1)[C@@H:13]1[O:20][C@H:17]([CH2:18][OH:19])[C@@H:15]([OH:16])[CH2:14]1.C(O)(=O)C>CS(C)=O>[CH2:2]([O:9][C:11]1[N:12]([C:21]2[N:22]=[C:23]([NH2:29])[NH:24][C:25](=[O:28])[C:26]=2[N:27]=1)[C@@H:13]1[O:20][C@H:17]([CH2:18][OH:19])[C@@H:15]([OH:16])[CH2:14]1)[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 244Benzyl AlcoholHCID 5360545Sodium2×HCID 13543712613389-03-2

Product 1

HCID 135476520HCID 135476520, compound

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent2×

Conditions

Temperature
65 °C

Procedure

Two hundred mL of dimethyl sulfoxide (DMSO) are added to a freshly prepared solution of sodium benzoylate (made from benzyl alcohol (75 mL) and sodium (2.14 g)) under an atmosphere of argon. 8-Bromodeoxyguanosine (10 g, 29 mmol) in DMSO (80 mL) is added to the resulting mixture and the reaction is heated to 65° C. for 24 hours. After cooling to room temperature, the reaction mixture is neutralized with glacial acetic acid and the DMSO is removed by vacuum distillation at 65° C. The remaining solution is poured into ether with stirring. The oily residue that remains after decanting off the ether is added to acetone and the resulting white precipitate is removed by filtration. After stirring with water, the slurry is filtered and the collected white solid recrystallized from methanol to give 8-(benzyloxy)-2'-deoxyguanosine.

Workup

  1. temperatureAfter cooling to room temperature
  2. customthe DMSO is removed by vacuum distillation at 65° C
  3. additionThe remaining solution is poured into ether
  4. customafter decanting off the ether
  5. additionis added to acetone
  6. customthe resulting white precipitate is removed by filtration
  7. stirringAfter stirring with water
  8. filtrationthe slurry is filtered
  9. customthe collected white solid recrystallized from methanol

Sources & evidence

ORD record
ord-0a13720327c7422eb3165958d032db2d
Source dataset
uspto-grants-2000_10
Patent number
US06132776

Reaction notes

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