Water → HCID 20637931, compound

Participants

Reaction Conditions

Reaction Steps

Cesium carbonate (0.72 g) and 4-(1,3,4)-oxadiazol-2-yl-phenol (0.54 g) were added to a solution of (4R)-4-[2-(pyridin-3-yl)ethyl]-1,3-dioxin-2-one (1.20 g, Example 14a)) in dry dimethylformamide (75 ml) and heated at 90° C. for 14 hours. After cooling, the reaction mixture was poured into water (50 ml) and extracted three times with ethyl acetate. The combined organic phases were extracted twice with 2M hydrochloric acid. The combined aqueous extracts were basified by dropwise addition of 2M aqueous sodium hydroxide and the aqueous solution was then extracted three times with ethyl acetate. The organic extracts were combined and dried over anhydrous magnesium sulfate, filtered and concentrated under reduced pressure. The residue was purified by normal phase HPLC eluting with 0 to 25% ethanol in dichloromethane to give the title compound as a solid (0.19 g).

Provenance & Evidence