反应详情

温度

25 °C

(R)-3-hydroxy-3-phenylpropionic acid (3.0 mmole) and 4-nitro phenylpiperazine (3 mmole) were dissolved in 20 mL of tetrahydrofuran at a room temperature, and EDC (6.0 mmole, 1-Ethyl-3-(3-dimethylaminopropyl)-carbodiimide) and HOBt (6 mmole, N-Hydroxybenzotriazole) were added dropwise to the mixture. Then, the resulting mixture was stirred at 25° C. for 5 hours. 20 mL of ethyl acetate was added three times to the mixture to extract an organic phase, and the prepared organic phase was dried over anhydrous magnesium sulfate (2 g), and filtered, and the resulting filtrate was concentrated under a reduced pressure, and purified with column chromatography (hexane:ethyl acetate=1:1). The resulting reaction product (1 mmol) was dissolved in methanol (20 mL), and subject to the reduction reaction at the presence of a palladium on charcoal (Pd/C) for 5 hours. The resulting reduction reaction product was concentrated under a reduced pressure to remove methanol, and extracted several times with ethyl acetate to separate an organic phase. The prepared organic phase was dried over anhydrous magnesium sulfate, and filtered, and the resulting filtrate was concentrated under a reduced pressure to obtain an intermediate reduced to an amino group (NH2). The intermediate reaction product prepared thus was dissolved in hydrofuran (10 mL), and 1,1′-carbodiimidazole (2 mmol) was added to the reaction product, and stirred at a room temperature for 1 hour. Then, excessive ammonium hydroxide was added to the resulting reaction mixture, and the reaction mixture was stirred at a room temperature for additional 2 hours. The resulting reaction mixture was diluted with water, and extracted several times with ethyl acetate to obtain an organic phase. The prepared organic phase was dried over magnesium sulfate, and concentrated under a reduced pressure. The resulting pellet was purified with column chromatography (hexane:ethyl acetate=1:1 to ethyl acetate) to obtain a title compound.

1. extractionto extract an organic phase
2. dry with materialthe prepared organic phase was dried over anhydrous magnesium sulfate (2 g)
3. filtrationfiltered
4. concentrationthe resulting filtrate was concentrated under a reduced pressure
5. custompurified with column chromatography (hexane:ethyl acetate=1:1)
6. customThe resulting reduction reaction product
7. concentrationwas concentrated under a reduced pressure
8. customto remove methanol
9. extractionextracted several times with ethyl acetate
10. customto separate an organic phase
11. dry with materialThe prepared organic phase was dried over anhydrous magnesium sulfate
12. filtrationfiltered
13. concentrationthe resulting filtrate was concentrated under a reduced pressure
14. customto obtain an intermediate
15. customThe intermediate reaction product
16. customprepared thus
17. stirringstirred at a room temperature for 1 hour
18. stirringthe reaction mixture was stirred at a room temperature for additional 2 hours
19. customThe resulting reaction mixture
20. extractionextracted several times with ethyl acetate
21. customto obtain an organic phase
22. dry with materialThe prepared organic phase was dried over magnesium sulfate
23. concentrationconcentrated under a reduced pressure
24. customThe resulting pellet was purified with column chromatography (hexane:ethyl acetate=1:1 to ethyl acetate)