Water → 3-Methyl-N-[(pent-4-en-1-yl)(propan-2-yl)carbamoyl]-L-valine

反応式

[CH:1]([N:4]([CH2:17][CH2:18][CH2:19][CH:20]=[CH2:21])[C:5]([NH:7][C@H:8]([C:13]([O:15]C)=[O:14])[C:9]([CH3:12])([CH3:11])[CH3:10])=[O:6])([CH3:3])[CH3:2].O.[Li+].[OH-]>O1CCOCC1>[CH:1]([N:4]([CH2:17][CH2:18][CH2:19][CH:20]=[CH2:21])[C:5]([NH:7][C@H:8]([C:13]([OH:15])=[O:14])[C:9]([CH3:12])([CH3:11])[CH3:10])=[O:6])([CH3:2])[CH3:3]

参加物

実験手順

To a solution (0.1 M) of methyl N-{[isopropyl(pent-4-en-1-yl)amino]carbonyl}-3-methyl-L-valinate in a 1:1 mixture of water and dioxane, LiOH (4 eq) was added and the resulting mixture was stirred at room temperature for 6 h. The reaction mixture was then concentrated at reduced pressure and the crude residue was dissolved in EtOAc. The organic phase was washed with water. The aqueous phase was brought to pH=2 and re-extracted with EtOAc. After drying over Na2SO4 and evaporation of the volatiles, N-{[isopropyl(pent-4-en-1-yl)amino]carbonyl}-3-methyl-L-valine was recovered as a brownish solid (100%) and used without any further purification. LRMS (ESI) m/z 285 [(M+H)+; calcd for C15H29N2O3: 285.2].