Phosphorus oxychloride → (S)-1-(4-Chloro-phenyl)-azetidine-2-carboxylic acid (5-tert-butyl-isoxazol-3-yl)-amide

Participants

Reaction Steps

To a cold solution (0° C.) of (S)-1-(4-Chloro-phenyl)-azetidine-2-carboxylic acid (100 mg; 0.472 mmol) and 3-amino-5-t-butylisoxazole (66 mg; 0.472 mmol) in pyridine (1.5 mL) is added phosphorus oxychloride (0.043 m; 0.48 mmol). The reaction mixture is stirred at room temperature for 18 hours. After this time, the reaction mixture is diluted with ethyl acetate and washed with diluted NH4Cl aqueous solution then brine, dried over Na2SO4, filtered and concentrated in vacuo. Purification by flash chromatography on silica gel using ethyl acetate/hexanes provides the title compound, m/z 334 [M+H+].

Provenance & Evidence