Reaction #1909792

Reaction equation

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

octadecylamine

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

→

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

Yield 87.1%

Solvents

dichloromethane

Conditions

Workup

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

Procedure

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%.

Source