Toluene → HCID 69099538, compound

Participants

Reaction Steps

A solution of ethyl 2-[4-(2-{[(E)-amino(hydroxyimino)methyl][4-(trifluoromethyl)benzyl]amino}ethyl)phenoxy]-2-methylpropanoate (1 g; 2.14 mmol) and triethylamine (0.30 ml; 2.14 mmol) in 10 ml of dichloromethane was cooled in an ice bath and treated under nitrogen with isobutyryl chloride (0.20 ml; 1.93 mmol). The mixture was allowed to warm to rt. After 1 hr, 8 ml of toluene were added and the reaction mixture was heated to 110C under a reflux condenser. After 5 hr, it was partitioned between ethyl acetate and 0.5N HCl. The organic phase was washed with 0.5 N HCl (twice), 1N NaOH (three times) and brine, dried over sodium sulfate and concentrated. Purification by flash chromatography using ethyl acetate-hexane mixtures (5–50% gradient) afforded ethyl 2-[4-(2-{(5-isopropyl-1,2,4-oxadiazol-3-yl)[4-(trifluoromethyl)benzyl]amino}ethyl)phenoxy]-2-methylpropanoate (470 mg; 43% yield).

Provenance & Evidence