Sodium Carbonate → HCID 57135198, compound

HRID 2184262Notes

Reaction equation

HRID 2184262 reaction equation
C([O:4][C@H:5]1[C@@H:9]([O:10]C(=O)C)[C@H:8]([N:14]2[CH:22]=[N:21][C:20]3[C:15]2=[N:16][C:17]([I:38])=[N:18][C:19]=3[NH:23][CH2:24][CH:25]([C:32]2[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=2)[C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)[O:7][C@@H:6]1[CH2:39][O:40]C(=O)C)(=O)C.C(=O)([O-])[O-].[Na+].[Na+]>O.CO>[C:32]1([CH:25]([C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)[CH2:24][NH:23][C:19]2[N:18]=[C:17]([I:38])[N:16]=[C:15]3[C:20]=2[N:21]=[CH:22][N:14]3[C@H:8]2[C@H:9]([OH:10])[C@H:5]([OH:4])[C@@H:6]([CH2:39][OH:40])[O:7]2)[CH:33]=[CH:34][CH:35]=[CH:36][CH:37]=1

Participants

4

Reactant 2

HCID 10340Sodium CarbonateHCID 20792644HCID 20792644, compound

Product 1

HCID 57135198HCID 57135198, compoundYield 100.5%

Reagents, catalysts & solvents 1

HCID 22242641Methanol--water (1/1)Solvent

Procedure

(2R,3R,4R,5R)-4-(Acetyloxy)-2-[(acetyloxy)methyl]-5-{6[(2,2-diphenylethyl)amino]-2-iodo-9H-purin-9-yl}tetrahydro-3-furanyl acetate (1.7 g, 2.43 mmol) (Preparation 1) was dissolved in 10:1, by volume, methanol water (88 ml). Solid sodium carbonate (1.5 g, 14.1 mmol) was added and the mixture stirred at room temperature for 90 minutes before removing the methanol by evaporation under reduced pressure. The residual aqueous solution was diluted with water (50 ml) and extracted with ethyl acetate (150 ml). The organic phase was washed sequentially with water and brine, dried over anhydrous sodium sulphate and the solvent removed under reduced pressure to yield the title compound as a white solid (1.4 g).

Workup

  1. custombefore removing the methanol
  2. customby evaporation under reduced pressure
  3. additionThe residual aqueous solution was diluted with water (50 ml)
  4. extractionextracted with ethyl acetate (150 ml)
  5. washThe organic phase was washed sequentially with water and brine
  6. dry with materialdried over anhydrous sodium sulphate
  7. customthe solvent removed under reduced pressure

Sources & evidence

ORD record
ord-5b6d8a7b685b4e6f98e078074b1ad31e
Source dataset
uspto-grants-2005_05
Patent number
US06900309B1

Reaction notes

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