Reaktion #1769161

ord-e30300e920b6491887b7b1cbfc7fa814

Reaktionsgleichung

C=CCCC(C[C@@H]1OC(=O)[C@H]1CCCCCC)OC(=O)[C@H](CC(C)C)NC=O
N-formyl-L-leucine 1-[(trans-3-hexyl-4-oxo-2-oxetanyl)methyl]-4-pentenyl ester
[H][H]
hydrogen
→
CCCCCC[C@@H]1C(=O)O[C@H]1CC(CCCC)OC(=O)[C@H](CC(C)C)NC=O
N-formyl-L-leucine 1-[(trans-3-hexyl-4-oxo2-oxetanyl]-methyl]pentyl ester

Edukte

C=CCCC(C[C@@H]1OC(=O)[C@H]1CCCCCC)OC(=O)[C@H](CC(C)C)NC=O
N-formyl-L-leucine 1-[(trans-3-hexyl-4-oxo-2-oxetanyl)methyl]-4-pentenyl ester
[H][H]
hydrogen

Reagenzien

[Pd]
Pd/C

Lösungsmittel

C1CCOC1
THF

Reaktionsbedingungen

Detaillierte Bedingungen
See reaction.notes.procedure_details.

Aufarbeitung

  1. 1
    Filtrationwas filtered off
  2. 2
    Sonstigethe filtrate was evaporated in vacuo
  3. 3
    SonstigeThe residue was chromatographed over silica gel with toluene/ethyl acetate (8:2)

Vorschrift

A solution of 10 mg of N-formyl-L-leucine 1-[(trans-3-hexyl-4-oxo-2-oxetanyl)methyl]-4-pentenyl ester in 0.5 ml of THF was treated with 2.5 mg of 5% Pd/C and hydrogenated. After the hydrogen uptake was finished the catalyst was filtered off and the filtrate was evaporated in vacuo. The residue was chromatographed over silica gel with toluene/ethyl acetate (8:2) and there was obtained amorphous N-formyl-L-leucine 1-[(trans-3-hexyl-4-oxo2-oxetanyl]-methyl]pentyl ester as a mixture of 2 diastereomers.

Quelle

DOI: 10.6084/m9.figshare.5104873.v1Patent: US05175186uspto-grants-1992_12