Sodium Bicarbonate → HCID 18650250, compound

Participants

Reaction Conditions

Reaction Steps

A solution of 3'-O-t-butyldimethylsilyl-4'-hydroxyiminomethylthymidine (1.98 g, 4.95 mM) the compounds of Formula 13, prepared, e.g., as described in Preparation 9) with NaOAc (7 mg, 0.09 mM) in Ac2O (7 ml) was stirred at 80° C. for 72 hours, allow to cool and treated with 10 g of ice followed by sat. NaHCO3. The solution was extracted CH2Cl2 (3×100 ml), and the organic phases were combined and dried over Na2SO4. The solvent was removed by evaporation and the residue was purified by flash column chromatography silica gel eluting with (20% acetone/CH2Cl2) affording 3'-O-t-butyldimethylsilyl-4'-cyano-5'-O-acetylthymidine (1.7 g, 4.0 mM). MP 67°-69° C.

Provenance & Evidence