Sodium Carbonate → HCID 53468206, compound

Participants

Reaction Steps

A mixture of the product from step C (82 mg, 0.15 mmol), 3-ethyl-1-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)imidazolidine-2,4-dione (which compound) (59 mg, 0.18 mmol, 1.2 equiv), sodium carbonate (48 mg, 0.45 mmol), and the palladium catalyst (0.12 mg, 0.015 mmol) in N,N-dimethylformamide/water (2:1, 2.1 mL) was heated at 80° C. under nitrogen for 4 h. The reaction was quenched with water (10 mL) and extracted with ethyl acetate (4×). The combined extracts were dried over sodium sulfate, passed through a short pad of silica gel, and concentrated. The coupling product obtained was then stirred overnight with 6 N HCl/methanol (20:1 v/v) at room temperature. The reaction mixture was concentrated to dryness and the residual material was purified by flash column chromatography (eluent: dichloromethane/methanol 100:0 to 90:10) to provide 1-(4-(2-chloro-5-((2S,3R,4R,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yl)benzyl)phenyl)-3-ethylimidazolidine-2,4-dione (47 mg, 47%).

Provenance & Evidence