Reaktion #449308

Reaktionsgleichung

N2-[(9-fluorenyl)methoxycarbonyl]-N1-[1(S)-(dimethoxymethyl)-3-butynyl]-L-leucinamide

piperidine

N-[(9-fluorenyl)methoxycarbonyl]-3-methyl-L-leucine

hydroxybenzotriazole

1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride

→

N2-[N-[(9-fluorenyl)methoxycarbonyl]-3-methyl-L-valyl]-N1-[1(S)-(dimethoxymethyl)-3-butynyl]-L-leucinamide

Lösungsmittel

dichloromethane

dichloromethane

Reaktionsbedingungen

Aufarbeitung

1. 1
   SonstigeThe mixture was evaporated to dryness
2. 2
   Sonstigethe residue was chromatographed on silica gel using firstly ethyl acetate/petrol (1:1)
3. 3
   Waschenmethanol/dichloromethane (1:9) for the elution
4. 4
   SonstigeEvaporation of the dichloromethane solution
5. 5
   Sonstigegave a gum which
6. 6
   Waschenwashed with 2Mhydrochloric acid and saturated sodium bicarbonate solution
7. 7
   Trocknendried over magnesium sulphate
8. 8
   Sonstigeevaporated to dryness
9. 9
   SonstigeThe residue was chromatographed on silica gel
10. 10
    Waschenfor the elution

Vorschrift

525 mg (1.1 mmol) of N2-[(9-fluorenyl)methoxycarbonyl]-N1-[1(S)-(dimethoxymethyl)-3-butynyl]-L-leucinamide were dissolved in 20 ml of dichloromethane and 5 ml of piperidine and the mixture was stirred at room temperature for 30 minutes.The mixture was evaporated to dryness and the residue was chromatographed on silica gel using firstly ethyl acetate/petrol (1:1) and then methanol/dichloromethane (1:9) for the elution. Evaporation of the dichloromethane solution gave a gum which was added to a solution of 363 mg (1.03 mmol) of N-[(9-fluorenyl)methoxycarbonyl]-3-methyl-L-leucine, 149mg (1.1 mmol) of hydroxybenzotriazole and 288 mg (1.5 mmol) of 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride in 15 ml of dichloromethane. The mixture was stirred for 18 hours, then washed with 2Mhydrochloric acid and saturated sodium bicarbonate solution, dried over magnesium sulphate and evaporated to dryness. The residue was chromatographed on silica gel using ethyl acetate/petrol (1:2) for the elution to give 501 mg of N2-[N-[(9-fluorenyl)methoxycarbonyl]-3-methyl-L-valyl]-N1-[1(S)-(dimethoxymethyl)-3-butynyl]-L-leucinamide as a white foam. MS: m/e 592.3 [M+H]+, 560.3 [M+H-MeOH]+.

Quelle