Reaktion #1909792

Reaktionsgleichung

N-[(9-fluorenyl)methoxycarbonyl]-L-isoleucine

octadecylamine

1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride

→

N-[(9-fluorenyl)methoxycarbonyl]-L-isoleucylaminooctadecane

Ausbeute 87.1%

Lösungsmittel

dichloromethane

Reaktionsbedingungen

Aufarbeitung

1. 1
   SonstigeThen, the obtained reaction mixture
2. 2
   Extraktionwas extracted with dichloromethane
3. 3
   Trocknenthe organic layer was dried over anhydrous magnesium sulfate
4. 4
   workup.DISTILLATIONThereafter, the solvent was distilled off under reduced pressure
5. 5
   Sonstigethe resultant residue was subjected to re-crystallization treatment
6. 6
   Filtrationwas subjected to a suction filtration

Vorschrift

2.47 g (0.007 mol) of N-[(9-fluorenyl)methoxycarbonyl]-L-isoleucine, 1.89 g (0.007 mol) of octadecylamine, 85.5 mg (0.0007 mol) of 4-(N,N-dimethylamino)pyridine (DMAP), and 1.61 g (0.0084 mol) of 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (EDC) was dissolved in 45 ml of dichloromethane, and the resultant solution was stirred for 4 days at room temperature. Then, the obtained reaction mixture was extracted with dichloromethane, and the organic layer was dried over anhydrous magnesium sulfate. Thereafter, the solvent was distilled off under reduced pressure, the resultant residue was subjected to re-crystallization treatment using ethyl acetate, and gel-like substance was subjected to a suction filtration, thereby obtaining 3.69 g of N-[(9-fluorenyl)methoxycarbonyl]-L-isoleucylaminooctadecane (hereinafter also referred to as “Intermediate product (1)”) at the yield of 87%.

Quelle