Reaktion #706186

Reaktionsgleichung

octadecylglycidyl ether

L-arginine

i-propanol

hydrochloric acid

octadecylglycidyl ether

→

N-(2-hydroxy-3-octadecyloxypropyl)-L-arginine hydrochloride

Ausbeute 42.3%

Lösungsmittel

water

Reaktionsbedingungen

Aufarbeitung

1. 1
   Temperaturover a period of 30 minutes while being heat-refluxed
2. 2
   workup.STIRRINGFurther, the mixture was stirred
3. 3
   Temperaturunder reflux for 3 hours
4. 4
   EinengenThe reaction solution was concentrated under reduced pressure
5. 5
   Sonstigethe residue was purified through silica-gel column chromatography (
6. 6
   workup.ADDITIONKieselgel 60, eluent=mixture of chloroform, methanol and acetic acid at a ratio of 3:1:0.5)

Vorschrift

L-arginine (17.4 g, 0.1 mols) was dissolved in 100 ml of water in a three-necked round flask, and 100 ml of i-propanol were added thereto. Then, 32.6 g (0.1 mols) of octadecylglycidyl ether (made by Sakamoto Yakuhin Kogyo Co., Ltd.) were added dropwise thereto over a period of 30 minutes while being heat-refluxed and stirred. Further, the mixture was stirred under reflux for 3 hours. It was identified through TLC and gas chromatography that octadecylglycidyl ether disappeared. Thereafter, the resulting mixture was neutralized with 10.1 g (0.1 mols) of 36% hydrochloric acid. The reaction solution was concentrated under reduced pressure, and the residue was purified through silica-gel column chromatography (Kieselgel 60, eluent=mixture of chloroform, methanol and acetic acid at a ratio of 3:1:0.5) to give 21.2 g of N-(2-hydroxy-3-octadecyloxypropyl)-L-arginine hydrochloride (yield 42.3%).

Quelle