1,2-Dichloroethane → HCID 58537216, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of 3-phenyl-4-propylisoxazole-5-carboxylic acid, lithium salt (23.12 mg, 0.1 mmol), (Z)-tert-butyl 1-(4-(N′-hydroxycarbamimidoyl)benzyl)azetidine-3-carboxylate, Int.1 (30.5 mg, 0.1 mmol), HOBT (16.85 mg, 0.110 mmol), diisopropylethylamine (0.044 mL, 0.250 mmol) and EDC (23.00 mg, 0.120 mmol) was stirred in DMF (1 mL) at rt for 18 hr. Additional EDC (23.00 mg, 0.120 mmol) was added and the reaction mixture was stirred at 60° C. for 5 hr. The reaction mixture was partitioned between EtOAc (30 mL) and saturated sodium bicarbonate solution (30 mL). The organic layer was washed with water (2×25 mL), brine (25 mL), dried (MgSO4) and concentrated to afford an oil that was chromatographed on a 4 gm Isco silica gel cartridge, eluting with a 0-50% EtOAc/Hex gradient. The essentially pure fractions containing product were concentrated to afford tert-butyl 1-(4-(5-(3-phenyl-4-propylisoxazol-5-yl)-1,2,4-oxadiazol-3-yl)benzyl)azetidine-3-carboxylate (22 mg, 0.044 mmol, 43.9% yield) as a colorless oil. HPLC retention time=1.84 minutes (PHENOMENEX® Luna 4.6×30 mm S-5 ODS column) eluting with 10-90% aqueous methanol+0.1% TFA over a 2 minute gradient. MS: (M+H)=501.21.

Provenance & Evidence