Imidazole → HCID 66625136, compound

Participants

Reaction Steps

A 250 mL round bottom flask was charged with N′-((2R,3S)-2-(3-chloro-4-cyano-2-propylphenylamino)-3-hydroxybutanoyl)-4-cyanobenzohydrazide (intermediate 1119-B) (0.710 g, 1.61 mmol) and THF (20 mL) at room temperature. Imidazole (0.440 g, 6.47 mmol) and tert-butyldimethyl silyl chloride (0.730 g, 4.84 mmol) were then added to the mixture which was stirred at room temperature for 48 h. Water (20 mL) was then added to the mixture followed by heptane (50 mL) and stirred for 30 min at room temperature. EtOAc (50 mL) was then added and the phases were partitioned. The organic extract was separated, dried over Na2SO4, and concentrated to furnish a yellow solid. The crude material was purified by flash column chromatography [SiO2, EtOAc-hexanes (20%:80%)→EtOAc-hexanes (50%:50%)→EtOAc-hexanes (60%:40%) as eluent] to afford the title compound as a light yellow solid with other minor impurities (0.750 g, 84% yield), which was immediately taken to the next synthetic step.

Provenance & Evidence