Triethylamine → HCID 66750899, compound

Participants

Reaction Steps

A mixture of 1-(2-tert-butylphenyl)piperazine dihydrochloride obtained in Reference Example 1 (1.13 g, 3.87 mmol), 3-hydroxyisoxazole-5-carboxylic acid (0.5 g, 3.87 mmol), triethylamine (1.39 mL, 10.0 mmol), EDCI (0.959 g, 5.0 mmol) and HOBt (0.766 g, 5.0 mmol) in N,N-dimethylformamide (15 mL) was stirred at room temperature for 16 h. Water was added to the reaction solution, and the mixture was extracted with ethyl acetate. The organic layer was washed with brine, dried over anhydrous magnesium sulfate, filtered and concentrated under reduced pressure to obtain an oil. A mixture of the obtained oil, tert-butyl bromoacetate (0.819 g, 4.2 mmol) and potassium carbonate (0.829 g, 6.0 mmol) in N,N-dimethylformamide (10 mL) was stirred at 50° C. for 16 h. Water was added to the reaction solution, and the mixture was extracted with ethyl acetate. The organic layer was washed with brine, dried over anhydrous magnesium sulfate, filtered and concentrated under reduced pressure to purify the residue by NH-silica gel column chromatography (hexane/ethyl acetate 90:10 to 40:60). Solvent was removed to afford oil (1.01 g, 59%).

Provenance & Evidence