Potassium Carbonate → HCID 59460393, compound

HRID 1713325Notes

Reaction equation

HRID 1713325 reaction equation
[Si]([O:8][C@@H:9]1[C@H:13]([O:14][Si](C(C)(C)C)(C)C)[C@@H:12]([CH2:22][O:23][Si](C(C)(C)C)(C)C)[O:11][C@H:10]1[N:31]1[C:40]2[N:39]=[CH:38][N:37]=[C:35]([NH2:36])[C:34]=2[N:33]=[C:32]1[NH:41][CH2:42][C:43]1[CH:48]=[CH:47][C:46]([C:49]2[CH:54]=[CH:53][CH:52]=[CH:51][C:50]=2[OH:55])=[CH:45][CH:44]=1)(C(C)(C)C)(C)C.C(=O)([O-])[O-].[K+].[K+].Br[CH2:63][C:64]([O:66][CH3:67])=[O:65]>CN(C)C=O>[CH3:67][O:66][C:64]([CH2:63][O:55][C:50]1[CH:51]=[CH:52][CH:53]=[CH:54][C:49]=1[C:46]1[CH:45]=[CH:44][C:43]([CH2:42][NH:41][C:32]2[N:31]([C:40]3[N:39]=[CH:38][N:37]=[C:35]([NH2:36])[C:34]=3[N:33]=2)[C@@H:10]2[O:11][C@H:12]([CH2:22][OH:23])[C@@H:13]([OH:14])[C@H:9]2[OH:8])=[CH:48][CH:47]=1)=[O:65]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 60984Methyl bromoacetateHCID 67456223HCID 67456223, compound

Product 1

HCID 59460393HCID 59460393, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 2′,3′,5′-tris-O-(tert-butyl-dimethylsilyl)-8-(2′-hydroxybiphenyl-4-ylmethylamino)-adenosine (0.313 g) in N,N-dimethylformamide (1.9 mL) was added potassium carbonate (0.080 g). Then methyl bromoacetate (0.048 mL) was added, and the resulting mixture was stirred at room temperature for 4 hours. The reaction mixture was partitioned between diethyl ether (35 mL) and water (10 mL). The organic layer was washed successively with water (10 mL×2) and brine (10 mL), dried over anhydrous sodium sulfate and concentrated under reduced pressure. The residue (0.337 g) was dissolved in methanol (1.7 mL). Ammonium fluoride (0.379 g) was added, and the resulting mixture was stirred at 60° C. for 19 hours. The reaction mixture was cooled to room temperature. Dichloromethane (10 mL) was added, and the insoluble material was filtered out. The filtrate was concentrated under reduced pressure and the residue was purified by column chromatography on silica gel (eluent: dichloromethane/methanol=10/1) to give the title compound (0.053 g).

Workup

  1. customThe reaction mixture was partitioned between diethyl ether (35 mL) and water (10 mL)
  2. washThe organic layer was washed successively with water (10 mL×2) and brine (10 mL)
  3. dry with materialdried over anhydrous sodium sulfate
  4. concentrationconcentrated under reduced pressure
  5. dissolutionThe residue (0.337 g) was dissolved in methanol (1.7 mL)
  6. additionAmmonium fluoride (0.379 g) was added
  7. stirringthe resulting mixture was stirred at 60° C. for 19 hours
  8. temperatureThe reaction mixture was cooled to room temperature
  9. additionDichloromethane (10 mL) was added
  10. filtrationthe insoluble material was filtered out
  11. concentrationThe filtrate was concentrated under reduced pressure
  12. customthe residue was purified by column chromatography on silica gel (eluent: dichloromethane/methanol=10/1)

Sources & evidence

ORD record
ord-46043eb55ade49bf97aba017e54c63d4
Source dataset
uspto-grants-2010_09
Patent number
US07795236B2

Reaction notes

Loading…