1,2-Dichloroethane → HCID 67459036, compound

Participants

Reaction Conditions

Reaction Steps

A solution of 4-(1,1-difluoroethyl)-5-phenylisoxazole-3-carboxylic acid (58.7 mg, 0.232 mmol), HOBt (64.0 mg, 0.418 mmol), and diisopropylethylamine (0.162 mL, 0.928 mmol) in acetonitrile (2 mL) was added EDC (105 mg, 0.545 mmol) and (Z)-tert-butyl 1-(4-(N′-hydroxycarbamimidoyl)benzyl)azetidine-3-carboxylate (Int.1, 70.8 mg, 0.232 mmol). The reaction mixture was stirred at 80° C. for 2 h and then concentrated. 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 gave 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