Reacción #72490

Ecuación de reacción

(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

Disolventes

water

—

solvent

Condiciones de reacción

Tratamiento posterior

1. 1
   workup.DISTILLATIONThe mixture was distilled under a reduced pressure
2. 2
   Otroto remove excessive solvents
3. 3
   workup.ADDITIONwas added to the resulting mixture
4. 4
   Otroto separate an organic phase
5. 5
   ExtracciónThen, the prepared organic phase was further extracted twice with 15 mL of ethyl acetate
6. 6
   SecadoThe organic phase was dried over anhydrous magnesium sulfate (2 g)
7. 7
   Filtraciónfiltered
8. 8
   Concentraciónthe resulting filtrate was concentrated under a reduced pressure
9. 9
   Otroseparated
10. 10
    Otropurified with column chromatography (hexane:ethyl acetate=1:1 to 1:10)
11. 11
    Otrothe resulting reaction mixture
12. 12
    workup.STIRRINGwas stirred at a room temperature for 1 hour
13. 13
    Otroresulting
14. 14
    Otroreaction mixture
15. 15
    workup.STIRRINGwas stirred at a room temperature for additional 2 hours
16. 16
    Extracciónextracted several times with ethyl acetate
17. 17
    Otroto obtain an organic phase
18. 18
    SecadoThe prepared organic phase was dried over magnesium sulfate
19. 19
    Concentraciónconcentrated under a reduced pressure
20. 20
    OtroThe resulting pellet was purified with column chromatography (hexane:ethyl acetate=1:1 to ethyl acetate)

Procedimiento

(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.

Fuente