Reaction #48508

Reaction equation

WSC

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

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

HOBt

→

title compound

Yield 61.0%

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

Yield 61.0%

Solvents

DMF

Conditions

Workup

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

Procedure

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.

Source