Реакция #72490

Уравнение реакции

(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

Растворители

water

—

solvent

Условия реакции

Обработка

1. 1
   workup.DISTILLATIONThe mixture was distilled under a reduced pressure
2. 2
   Другоеto remove excessive solvents
3. 3
   workup.ADDITIONwas added to the resulting mixture
4. 4
   Другоеto separate an organic phase
5. 5
   ЭкстракцияThen, the prepared organic phase was further extracted twice with 15 mL of ethyl acetate
6. 6
   СушкаThe organic phase was dried over anhydrous magnesium sulfate (2 g)
7. 7
   Фильтрацияfiltered
8. 8
   Концентрированиеthe resulting filtrate was concentrated under a reduced pressure
9. 9
   Другоеseparated
10. 10
    Другоеpurified with column chromatography (hexane:ethyl acetate=1:1 to 1:10)
11. 11
    Другоеthe resulting reaction mixture
12. 12
    workup.STIRRINGwas stirred at a room temperature for 1 hour
13. 13
    Другоеresulting
14. 14
    Другоеreaction mixture
15. 15
    workup.STIRRINGwas stirred at a room temperature for additional 2 hours
16. 16
    Экстракцияextracted several times with ethyl acetate
17. 17
    Другоеto obtain an organic phase
18. 18
    СушкаThe prepared organic phase was dried over magnesium sulfate
19. 19
    Концентрированиеconcentrated under a reduced pressure
20. 20
    ДругоеThe resulting pellet was purified with column chromatography (hexane:ethyl acetate=1:1 to ethyl acetate)

Методика

(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.

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