Methyl iodide → HCID 11348311, Verbindung

Reaktionsgleichung

[CH2:1]([O:8][C:9]([NH:11][C@H:12]([CH2:22][OH:23])[CH2:13][CH2:14][C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:24]I>C(#N)C.[Ag]=O>[CH2:1]([O:8][C:9]([NH:11][C@H:12]([CH2:22][O:23][CH3:24])[CH2:13][CH2:14][C:15]([O:17][C:18]([CH3:19])([CH3:20])[CH3:21])=[O:16])=[O:10])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Komponenten

Versuchsvorschrift

To a solution of tert-butyl (4S)-4-{[(benzyloxy)carbonyl]amino}-5-hydroxypentanoate (4.0 g, 12.4 mmol) in acetonitrile (80 ml) were added silveroxide (14.3 g, 61.7 mmol) and methyliodide (7.7 ml, 124 mmol), and the mixture was stirred for 19 hours. After removal of the insoluble materials, the solvent was removed in vacuo and the residue was purified with silica gel chromatography to give tert-butyl (4S)-4-{[(benzyloxy)carbonyl]amino}-5-methoxypentanoate (2.98 g, 71%).