Imidazole → HCID 9948972, compound

Participants

Reaction Conditions

Reaction Steps

A solution of imidazole (42 mg) in dry DMF (5 mL) is treated with 60% sodium hydride dispersion in mineral oil (25 mg), stirred for 3 minutes and treated with (-)-5-(acetamidomethyl)-3-(3,4,5-trifluorophenyl)isoxazoline (see Example 25) (150 mg). After 18 hours, the mixture is heated to 40° C. for 2 hours. TLC analysis (5% CH3OH--CH2Cl2) indicated the reaction to be virtually complete. The mixture is diluted with water (50 mL) and extracted with EtOAc (6×20 mL), dried over Na2SO4, filtered and concentrated under reduced pressure to give a white solid. Chromatography over silica (radial chromatography, 2 mm plate) eluting with CH2Cl2, 2% and 5% CH3OH--CH2Cl2 gives 100 mg of the title compound as a white solid, mp 168-169° C., [α]25D -80° (c 0.61, DMSO).

Provenance & Evidence