Reaktion #6163

Reaktionsgleichung

N-[(benzyloxy)carbonyl]-L-leucine (S)-1-[[(2S,3S)-3-ethyl-4-oxo-2-oxetanyl]methyl]octadecyl ester

→

N-formyl-(S)-leucine (S)-1-[[(2S,3S)-3-ethyl-4-oxo-2-oxetanyl]methyl]octadecyl ester

Lösungsmittel

THF

Reaktionsbedingungen

Aufarbeitung

1. 1
   Filtrationwas filtered off
2. 2
   Sonstigethe filtrate was evaporated
3. 3
   workup.ADDITION71 μl of formic acid/acetic acid anhydride were added dropwise
4. 4
   workup.ADDITIONThe mixture was diluted with 5 ml of diethyl ether
5. 5
   Waschenwashed twice with 2% sodium hydrogen carbonate solution
6. 6
   TrocknenAfter drying over sodium sulfate it
7. 7
   Filtrationwas filtered
8. 8
   Sonstigeevaporated
9. 9
   SonstigeBy chromatography on silica gel and recrystallization from n-pentane

Vorschrift

565 mg of N-[(benzyloxy)carbonyl]-L-leucine (S)-1-[[(2S,3S)-3-ethyl-4-oxo-2-oxetanyl]methyl]octadecyl ester were dissolved in 12 ml of THF. The mixture was hydrogenated at room temperature in the presence of 40 mg of 10% Pd/C. After the reaction was finished the catalyst was filtered off and the filtrate was evaporated. The residue was taken up in 9 ml of THF and 71 μl of formic acid/acetic acid anhydride were added dropwise. The mixture was diluted with 5 ml of diethyl ether and washed twice with 2% sodium hydrogen carbonate solution and then with water. After drying over sodium sulfate it was filtered and evaporated. By chromatography on silica gel and recrystallization from n-pentane there was obtained N-formyl-(S)-leucine (S)-1-[[(2S,3S)-3-ethyl-4-oxo-2-oxetanyl]methyl]octadecyl ester of m.p. 60°-61° C.

Quelle