反应详情

温度

80 °C

To a solution of 4-isopropyl-5-(pyridin-2-yl)isoxazole-3-carboxylic acid salt (10.4 mg, approx. 0.045 mmol), HOBt (12.34 mg, 0.081 mmol), and diisopropylethylamine (0.031 mL, 0.179 mmol) in acetonitrile (1 mL) was added EDC (20.2 mg, 0.105 mmol) and tert-butyl 1-(4-(N′-hydroxycarbamimidoyl)benzyl)azetidine-3-carboxylate, Int. 1 (13.68 mg, 0.045 mmol). The reaction mixture was stirred at 80° C. for 5 h. The reaction 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. Concentration followed by purification on a preparative TLC plate with ethyl acetate afforded tert-butyl 1-(4-(5-(4-isopropyl-5-(pyridin-2-yl)isoxazol-3-yl)-1,2,4-oxadiazol-3-yl)benzyl)azetidine-3-carboxylate.

1. concentrationThe reaction mixture was concentrated
2. additionthe residue was diluted with ethyl acetate (3 mL)
3. washwashed with a saturated aqueous solution of sodium bicarbonate (1 mL)
4. washwashed with water (1 mL)
5. washwashed with brine (1 mL)
6. dry with materialdried over anhydrous sodium sulfate
7. concentrationConcentration
8. customfollowed by purification on a preparative TLC plate with ethyl acetate