Reaktion #576249

Reaktionsgleichung

sodium hydrogencarbonate

benzyl 3-(N-FMOC-L-valyloxy)-2-hydroxypropionate

pyridine

stearoylchloride

→

Benzyl 3-(N-FMOC-L-valyloxy)-2-stearoyloxypropionate

Lösungsmittel

dichloromethane

dichloromethane

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.STIRRINGthe mixture stirred for 30 minutes
2. 2
   SonstigeThe organic phase was seperated
3. 3
   Extraktionthe water phase was extracted two times with dichloromethane
4. 4
   TrocknenThe combined organic phases were dried with sodium sulfate
5. 5
   Einengenconcentrated in vacuo
6. 6
   SonstigeThe product was isolated by silica gel chromatography

Vorschrift

To a stirred solution of benzyl 3-(N-FMOC-L-valyloxy)-2-hydroxypropionate (4.6 g 8.89 mmole) and pyridine (1.41 g, 17.8 mmole) in 80 ml dichloromethane was added dropwise a solution of stearoylchloride (3.64 g, 12 mmole) in 20 ml dichloromethane and the mixture was stirred overnight at room temperature. 100 ml of 5% sodium hydrogencarbonate solution was added and the mixture stirred for 30 minutes. The organic phase was seperated and the water phase was extracted two times with dichloromethane. The combined organic phases were dried with sodium sulfate and concentrated in vacuo. The product was isolated by silica gel chromatography. Yield: 6.1 g=87%

Quelle