Reacción #48508

Ecuación de reacción

WSC

1-(Piperazin-1-yl)tetrahydropyrimidin-2(1H)-one

(2S)-3-[(6-chloronaphthalen-2-yl)sulfony]-2-hydroxypropionic acid

HOBt

→

title compound

Rendimiento 61.0%

1-(4-{(2S)-3-[(6-Chloronaphthalen-2-yl)sulfonyl]-2-hydroxypropanoyl}piperazin-1-yl)tetrahydropyrimidin-2(1H)-one

Rendimiento 61.0%

Disolventes

DMF

Condiciones de reacción

Tratamiento posterior

1. 1
   ConcentraciónThe reaction mixture was concentrated under reduced pressure
2. 2
   Lavadothe residue was washed with an aqueous sodium bicarbonate solution
3. 3
   Extracciónextracted with dichloromethane
4. 4
   SecadoThe extract was dried over sodium sulfate
5. 5
   workup.DISTILLATIONthe solvent was distilled off under reduced pressure
6. 6
   OtroThe residue was purified by basic silica gel column chromatography (ethyl acetate to ethyl acetate/methanol=5/1)
7. 7
   Otrorecrystallized from ethyl acetate-methanol

Procedimiento

1-(Piperazin-1-yl)tetrahydropyrimidin-2(1H)-one obtained in Example 25b) (0.55 g), (2S)-3-[(6-chloronaphthalen-2-yl)sulfony]-2-hydroxypropionic acid (0.94 g) and HOBt (0.46 g) were dissolved in DMF (20 mL), WSC was added thereto, and the mixture was stirred at room temperature for 15 hours. The reaction mixture was concentrated under reduced pressure, and the residue was washed with an aqueous sodium bicarbonate solution, and extracted with dichloromethane. The extract was dried over sodium sulfate, and the solvent was distilled off under reduced pressure. The residue was purified by basic silica gel column chromatography (ethyl acetate to ethyl acetate/methanol=5/1), and recrystallized from ethyl acetate-methanol to obtain the title compound (0.88 g, 61%) as a colorless powder.

Fuente