Imidazole → HCID 9926419, compound

Participants

Reaction Conditions

Reaction Steps

Imidazole (225 mg) is dissolved in 5 ml dimethylformamide in a 25 ml one neck round bottom flask under nitrogen. The solution is cooled to 0° C., is treated with 60% sodium hydride (132 mg), and the mixture is stirred 20 minutes at room temperature. The solution is treated with (-)-5-(acetamidomethyl)-3-(3,4-difluorophenyl)-isoxazoline (Step 1, Example 11) (763 mg), and the reaction is stirred 6 hours at 65° C. The reaction is cooled, is diluted with 25 ml ethyl acetate, and is washed with 4×25 ml 50% saturated 1:1 sodium chloride/sodium bicarbonate. The organics are dried over anhydrous magnesium sulfate and are concentrated in vacuo to a white solid. The crude material is chromatographed over 25 g silica gel (230-400 mesh), eluting with 4% methanol/dichloromethane while collecting 5 ml fractions. Fractions 33-69 are combined and concentrated to give 256 mg of a white solid which is washed with ethyl acetate to afford 227 mg (25%) of the title compound as a white solid, mp 155-156° C, [α]25D -76° (c 0.30).

Provenance & Evidence