反应详情

A solution of 3-chloro-4-fluorocinnamic acid (4.52 g, 21.9 mmol), (S)-1-(3-hydroxy-propyl)-3-methyl-piperazin-2-one (3.76 g, 21.9 mmol), N,N-diisopropylethylamine (8.46 g, 65.5 mmol), 1-hydroxybenzotriazole (3.25 g, 24.0 mmol), and N-ethyl-N′-(3-dimethylaminopropyl)carbodiimide hydrochloride (4.60 g, 24.0 mmol) in N,N-dimethylformamide (80 ml) was stirred at room temperature for 18 h, then partitioned between 1 M aq. hydrochloric acid solution and ethyl acetate. The organic layer was washed with 1 M aq. hydrochloric acid solution, sat. aq. sodium hydrogencarbonate solution, and brine, dried (MgSO4), filtered, and evaporated. Chromatography (SiO2; CH2Cl2/MeOH/NH4OH 90:10:0.25) produced the title compound (6.54 g, 84%). Colorless gum, MS (ISP)=355.2 (M+H)+.

1. custompartitioned between 1 M aq. hydrochloric acid solution and ethyl acetate
2. washThe organic layer was washed with 1 M aq. hydrochloric acid solution, sat. aq. sodium hydrogencarbonate solution, and brine
3. dry with materialdried (MgSO4)
4. filtrationfiltered
5. customevaporated