Reaktion #622128

Reaktionsgleichung

sodium hydrogen carbonate

[4-(2-tert-butylphenyl)piperazin-1-yl](oxo)acetic acid

2-[4-(2-tert-butylphenyl)piperazin-1-yl]-2-oxoacetic acid

benzyl glycinate hydrochloride

EDCI

HOBt

triethylamine

→

benzyl N-{[4-(2-tert-butylphenyl)piperazin-1-yl](oxo)acetyl}glycinate

Ausbeute 83.2%

Lösungsmittel

acetonitrile

Reaktionsbedingungen

Aufarbeitung

1. 1
   Extraktionextracted with ethyl acetate
2. 2
   WaschenThe organic layer was washed with saturated sodium hydrogen carbonate solution and brine
3. 3
   Trocknendried over MgSO4
4. 4
   Sonstigethe solvent was evaporated under reduced pressure
5. 5
   Sonstigeto give the crude product
6. 6
   SonstigeThe product was purified by flash column chromatography (silica gel, n-hexane/ethyl acetate=90:10 to 50:50)

Vorschrift

A solution of [4-(2-tert-butylphenyl)piperazin-1-yl](oxo)acetic acid (Example 44, 0.300 g, 1.03 mmol), benzyl glycinate hydrochloride (0.250 g, 1.24 mmol), EDCI (0.238 g, 1.24 mmol), HOBt (0.168 g, 1.24 mmol) and triethylamine (201 μL, 1.44 mmol) in acetonitrile (10 mL) was stirred at room temperature for 2 days. The reaction mixture was poured into saturated sodium hydrogen carbonate solution and extracted with ethyl acetate. The organic layer was washed with saturated sodium hydrogen carbonate solution and brine, dried over MgSO4, and the solvent was evaporated under reduced pressure to give the crude product. The product was purified by flash column chromatography (silica gel, n-hexane/ethyl acetate=90:10 to 50:50) to provide benzyl N-{[4-(2-tert-butylphenyl)piperazin-1-yl](oxo)acetyl}glycinate (0.375 g, 83%) as a white powder.

Quelle