1,2-Dichloroethane → HCID 67459028, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of 5-phenyl-4-(3,3,3-trifluoropropyl)isoxazole-3-carboxylic acid (5 mg, 0.018 mmol), HOBt (4.83 mg, 0.032 mmol) and diisopropylethylamine (12.3 μL, 0.070 mmol) in acetonitrile (0.5 mL) was added EDC (7.90 mg, 0.041 mmol) and (Z)-tert-butyl 1-(4-(N′-hydroxycarbamimidoyl)benzyl)azetidine-3-carboxylate (Int.1, 5.35 mg, 0.018 mmol). The reaction mixture was stirred at 23° C. for 2.5 h. The mixture was concentrated, and the residue was diluted with ethyl acetate (3 mL), washed with a saturated aqueous solution of sodium bicarbonate (1 mL), washed with water (1 mL), washed with brine (1 mL), and dried over anhydrous sodium sulfate. The mixture was concentrated and dissolved in acetonitrile (0.5 mL). A 1M solution of tetrabutylammonium fluoride in tetrahydrofuran (35 μL, 0.035 mmol) was added, and the reaction mixture was stirred for 1 h. The reaction mixture was concentrated, and the residue was diluted with ethyl acetate (3 mL), washed with water (1 mL), washed with a saturated aqueous solution of sodium carbonate (1 mL), washed with brine (1 mL), and dried over anhydrous sodium sulfate. Concentration followed by purification on a preparative TLC plate with hexanes/ethyl acetate (7/3) afforded tert-butyl 1-(4-(5-(5-phenyl-4-(3,3,3-trifluoropropyl)isoxazol-3-yl)-1,2,4-oxadiazol-3-yl)benzyl)azetidine-3-carboxylate.

Provenance & Evidence