反应详情

温度

80 °C

A solution of 4-tert-butyl-5-phenylisoxazole-3-carboxylic acid (25 mg, 0.102 mmol), HOBt (28.1 mg, 0.183 mmol), and diisopropylethylamine (0.071 mL, 0.408 mmol) in acetonitrile (1 mL) was added EDC (45.9 mg, 0.240 mmol) and (Z)-tert-butyl 1-(4-(N′-hydroxycarbamimidoyl)benzyl)azetidine-3-carboxylate (Int.1, 31.1 mg, 0.102 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 by preparative HPLC afforded tert-butyl 1-(4-(5-(4-tert-butyl-5-phenylisoxazol-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 by preparative HPLC