Hydrochloric Acid → HCID 66588882, compound

Participants

Reaction Conditions

Reaction Steps

To ethyl 2-(((benzyloxycarbonyl)(methyl)amino)(3-(hydroxymethyl)cyclopentyl)methyl)-5-hydroxy-6-oxo-1,6-dihydropyrimidine-4-carboxylate (0.235 g, 0.511 mmol)in THF (30 mL) at 0° C. was added triethylamine (0.214 mL, 1.53 mmol) and methanesulfonyl chloride (0.119 mL, 1.53 mmol). The reaction mixture was stirrer at 23° C. for 3 hours. H2O (50 mL) was then added and the reaction mixture extracted with ethyl acetate (3×50 mL). The combined organic fractions were dried (MgSO4) and concentrated in vacuo. LCMS (+ESI, M+H+) m/z 694. To the crude ethyl 2-(((benzyloxycarbonyl)(methyl)amino)(3-((methylsulfonyloxy)methyl)cyclopentyl)methyl)-1-(methylsulfonyl)-5-(methylsulfonyloxy)-6-oxo-1,6-dihydropyrimidine-4-carboxylate (0.252 g, 0.363 mmol) dissolved in DMF (40 mL) was added Cs2CO3 (0.590 g, 1.816 mmol). The reaction mixture was stirred at 80° C. for 12 hours. HCl (1N, 40 ml) was added and the organic material was extracted with ethyl acetate (3×30 mL). The combined organic fractions were dried (MgSO4) and concentrated in vacuo to afford the title compound. LCMS (+ESI, M+H+) m/z 442.

Provenance & Evidence