Reacción #1909792

Ecuación de reacción

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

octadecylamine

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

→

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

Rendimiento 87.1%

Disolventes

dichloromethane

Condiciones de reacción

Tratamiento posterior

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

Procedimiento

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%.

Fuente