Chlorotrimethylsilane → 3'-O-allyl-N6-benzoyl Adenosine

HRID 23242Notes

Reaction equation

HRID 23242 reaction equation
[CH2:1]([O:4][C@@H:5]1[C@@H:9]([CH2:10][OH:11])[O:8][C@@H:7]([N:12]2[C:21]3[N:20]=[CH:19][N:18]=[C:16]([NH2:17])[C:15]=3[N:14]=[CH:13]2)[C@@H:6]1[OH:22])[CH:2]=[CH2:3].O=P12OP3(OP(OP(O3)(O1)=O)(=O)O2)=O.C[Si](C)(C)Cl.[C:42](Cl)(=[O:49])[C:43]1[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=1.[NH4+].[OH-]>N1C=CC=CC=1.O>[CH2:1]([O:4][C@@H:5]1[C@@H:9]([CH2:10][OH:11])[O:8][C@@H:7]([N:12]2[C:21]3[N:20]=[CH:19][N:18]=[C:16]([NH:17][C:42](=[O:49])[C:43]4[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=4)[C:15]=3[N:14]=[CH:13]2)[C@@H:6]1[OH:22])[CH:2]=[CH2:3]

Participants

8

Reactant 5

HCID 6397ChlorotrimethylsilaneHCID 7412Benzoyl chloride2×HCID 14812Phosphorus oxide (P4O10)HCID 14923Ammonium HydroxideHCID 110012923'-O-Allyladenosine

Product 1

HCID 110478913'-O-allyl-N6-benzoyl AdenosineYield 62%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 1049PyridineSolvent

Procedure

2′/3′-O-allyl adenosine (15.19 g, 51.1 mmol) was dried over P2O5 under high vacuum overnight at 40° C. It was then dissolved in anhydrous pyridine (504.6 mL) under inert atmosphere. Trimethylchlorosilane (32.02 mL, 252.3 mmol) was added at 0° C. and the reaction mixture was stirred for 1 hr under inert atmosphere. Then benzoyl chloride (29.4 mL, 252.3 mmol) was added dropwise. Once the addition of benzoyl chloride was over, the reaction mixture was brought to room temperature and stirred for 4 hrs. Then the reaction mixture was brought to 0° C. in an ice bath. Water (100.9 mL) was added and the reaction mixture was stirred for 30 minutes. Then NH4OH (100.0 mL, 30% aqueous solution w/w) was added, keeping the reaction mixture at 0° C. and stirring for an additional 1 hr. Solvent evaporated residue partitioned between water and ether. Product precipitates as an oil, which was then chromatographed (5% MeOH in CH2Cl2) to get the title compound as a white foam (12.67 g, 62%).

Workup

  1. customwas brought to room temperature
  2. stirringstirred for 4 hrs
  3. customThen the reaction mixture was brought to 0° C. in an ice bath
  4. stirringthe reaction mixture was stirred for 30 minutes
  5. customat 0° C.
  6. stirringstirring for an additional 1 hr
  7. customSolvent evaporated residue
  8. custompartitioned between water and ether
  9. customProduct precipitates as an oil, which
  10. customwas then chromatographed (5% MeOH in CH2Cl2)

Sources & evidence

ORD record
ord-507d08c893fa43438ae148c37145f8eb
Source dataset
uspto-grants-2005_02
Patent number
US06849723B2

Reaction notes

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