Dimethylformamide → HCID 25028948, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of (4R)-3-[4-(4-bromophenyl)-1,3-thiazol-2-yl]-4-ethyl-1,3-oxazolidin-2-one (1.46 g, 4.13 mmol), prepared in step 2 of Example 9, in dry DMF (15 mL) was added zinc cyanide (0.266 g, 2.27 mmol) and tetrakis(triphenylphosphine)palladium (0) (150 mg), under nitrogen, and the mixture heated to 145° C. After 1 h, the mixture was cooled to room temperature, diluted with ethyl acetate, which was then washed with water, brine, dried (anhydrous sodium sulfate) and evaporated. The residue was purified by silica gel column chromatography (ethyl acetate:hexanes, gradient elution) to afford the title compound (0.67 g, 54%), mp 153-157° C., MS m/z 300 [M+H]+. ANLC 100% at 210-370 nm, 9.5 min; 100% at 240 nm, 9.5 min, Xterra® RP18 column, 3.5μ, 150×4.6 mm column, 1.2 mL/min, 85/15-5/95 (Ammon. Form. Buff. pH=3.5/ACN+MeOH) for 10 min, hold 4 min.

Provenance & Evidence