Triethylamine → Tert-butyl 1-(3-chloro-4-(5-(3-phenyl-4-(trifluoromethyl)isoxazol-5-yl)-1,2,4-oxadiazol-3-yl)benzyl)azetidine-3-carboxylate

Participants

Reaction Steps

A mixture of 3-phenyl-4-(trifluoromethyl)isoxazole-5-carboxylic acid (1-D, 0.027 g, 0.105 mmol), tert-butyl 1-(3-chloro-4-(N′-hydroxycarbamimidoyl)benzyl)azetidine-3-carboxylate (0.036 g, 0.105 mmol), BOP-Cl (0.035 g, 0.136 mmol), and triethylamine (0.044 mL, 0.315 mmol) in N,N-dimethylformamide (1 mL) was shaken on platform shaker at room temperature overnight. The reaction mixture was diluted with dichloromethane, washed with a saturated aqueous solution of sodium bicarbonate, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The crude product was loaded on a fitted funnel containing a pad of CELITE® topped with a pad of silica gel, eluted with a 5% mixture of ethyl acetate in hexane, eluted with dichloromethane, and then eluted with a 20% mixture of ethyl acetate in hexane to give tert-butyl 1-(3-chloro-4-(5-(3-phenyl-4-(trifluoromethyl)isoxazol-5-yl)-1,2,4-oxadiazol-3-yl)benzyl)azetidine-3-carboxylate (0.013 g, 0.023 mmol, 22% yield) as a white solid. The compound had an HPLC ret. time=2.13 min.−Column. CHROMOLITH® SpeedROD 4.6×50 mm (4 min.); Solvent A=10% MeOH, 90% H2O, 0.1% TFA; Solvent B=90% MeOH, 10% H2O, 0.1% TFA. MS M+1=561.2.

Provenance & Evidence