反応 #72490

反応方程式

(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

溶媒

water

—

solvent

反応条件

後処理

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

実験手順

(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.

出典