反应 #72490

反应方程式

(R)-3-hydroxy-3-phenylpropionic acid

3,4-dimethoxy phenyl piperazine

tetrahydrofuran

phenethylamine

tetrahydrofuran

EDC

HOBt

→

title compound

Phenethyl-carbamic acid-(R)-3-[4-(3,4-dimethoxy-phenyl)-piperazin-1-yl]-3-oxo-1-phenyl-propyl ester

溶剂

water

—

solvent

反应条件

后处理

1. 1
   workup.DISTILLATIONThe mixture was distilled under a reduced pressure
2. 2
   其他to remove excessive solvents
3. 3
   workup.ADDITIONwas added to the resulting mixture
4. 4
   其他to separate an organic phase
5. 5
   萃取Then, the prepared organic phase was further extracted twice with 15 mL of ethyl acetate
6. 6
   干燥The organic phase was dried over anhydrous magnesium sulfate (2 g)
7. 7
   过滤filtered
8. 8
   浓缩the resulting filtrate was concentrated under a reduced pressure
9. 9
   其他separated
10. 10
    其他purified with column chromatography (hexane:ethyl acetate=1:1 to 1:10)
11. 11
    其他the resulting reaction mixture
12. 12
    workup.STIRRINGwas stirred at a room temperature for 1 hour
13. 13
    其他resulting
14. 14
    其他reaction mixture
15. 15
    workup.STIRRINGwas stirred at a room temperature for additional 2 hours
16. 16
    萃取extracted several times with ethyl acetate
17. 17
    其他to obtain an organic phase
18. 18
    干燥The prepared organic phase was dried over magnesium sulfate
19. 19
    浓缩concentrated under a reduced pressure
20. 20
    其他The resulting pellet was purified with column chromatography (hexane:ethyl acetate=1:1 to ethyl acetate)

实验过程

(R)-3-hydroxy-3-phenylpropionic acid (1.0 g, 6.0 mmole) and 3,4-dimethoxy phenyl piperazine (1.18 g, 6.0 mmole) were dissolved in 50 mL of a solvent ‘tetrahydrofuran at a room temperature, and EDC (1.24 g, 6.0 mmole) and HOBt (0.81 g, 6 mmole) were added dropwise to the mixture. Then, the resulting mixture was stirred at 25° C. for 5 hours. The mixture was distilled under a reduced pressure to remove excessive solvents, and the solvent-free mixture was neutralized with 1 normal aqueous sodium chloride solution (20 mL), and 25 mL of ethyl acetate was added to the resulting mixture to separate an organic phase. Then, the prepared organic phase was further extracted twice with 15 mL of ethyl acetate. The organic phase was dried over anhydrous magnesium sulfate (2 g), and filtered, and the resulting filtrate was concentrated under a reduced pressure, and separated and purified with column chromatography (hexane:ethyl acetate=1:1 to 1:10). The resulting reaction product (0.345 g, 1 mmol) was dissolved in tetrahydrofuran (15 mL), and 1,1′-carbodiimidazole (0.325 g, 2 mmol) was then added to the reaction product, and the resulting reaction mixture was stirred at a room temperature for 1 hour. Then, excessive phenethylamine was added to the reaction mixture, and resulting reaction mixture was stirred at a room temperature for additional 2 hours. The 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.

来源