Tetrahydrofuran → HCID 67459036, compound

Participants

Reaction Steps

To a solution of 4-(1,1-difluoropropyl)-5-phenylisoxazole-3-carbonyl fluoride (7.2 mg, 0.027 mmol) and (Z)-tert-butyl 1-(4-(N′-hydroxycarbamimidoyl)benzyl)azetidine-3-carboxylate (Int.1, 8.17 mg, 0.027 mmol) in acetonitrile (1 mL) was added Hunig's Base (9.34 μL, 0.053 mmol), and the reaction mixture was stirred at room temperature for 3 days. The reaction mixture was concentrated and diluted with ethyl acetate (3 ml), washed with water (1 mL), washed with a saturated aqueous solution of sodium carbonate (1 mL), washed brine (1 mL), and dried over anhydrous sodium sulfate. The mixture was concentrated, dissolved in acetonitrile (1 mL), and a 1M solution of tetrabutylammonium fluoride in tetrahydrofuran (53 μL, 0.053 mmol) was added. The reaction mixture was stirred at room temperature for 5 h. The reaction mixture was concentrated, diluted with ethyl acetate (3 ml), washed with water (1 ml), washed with a saturated aqueous solution of sodium bicarbonate (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-(1,1-difluoropropyl)-5-phenylisoxazol-3-yl)-1,2,4-oxadiazol-3-yl)benzyl)azetidine-3-carboxylate.

Provenance & Evidence