Methanol → HCID 89650724, compound

Participants

Reaction Steps

To a solution of chiral 1-((2R,3R,4S,5S)-3,5-difluoro-4-hydroxy-5-(hydroxymethyl)-3-methyltetrahydrofuran-2-yl)pyrimidine-2,4(1H,3H)-dione (42 mg, 151 μmol) prepared in Preparation 6 in THF (8.00 ml) was added a THF solution (Aldrich, 1 M) of tert-butylmagnesium chloride (377 μl, 377 μmol) dropwise. The mixture was stirred at room temperature for 15 min. followed by the addition of THF solution (0.5 M) of (2S)-isopropyl 2-(chloro(phenoxy)phosphorylamino)propanoate (755 μl, 377 μmol). The reaction mixture was stirred at room temperature for 1 hr, followed by the addition of THF solution (Aldrich, 1 M) of tert-butylmagnesium chloride (189 μl, 189 μmol) and THF solution (0.5 M) of (2S)-isopropyl 2-(chloro(phenoxy)phosphorylamino)propanoate (378 μl, 189 μmol). The reaction mixture was then stirred at room temperature for 2 h. Methanol (2 mL) was added to quench the reaction, The mixture was purified by flash chromatography (silica gel, 0-15% MeOH in DCM) and dried in vacuo to give the title compound as a light-yellow solid (18 mg, 22%).

Provenance & Evidence