Lithium Hydroxide → 3-Methyl-N-[methyl(pent-4-en-1-yl)carbamoyl]-L-valine
Reaktionsgleichung
[CH3:1][C:2]([CH3:19])([CH3:18])[C@@H:3]([C:14]([O:16]C)=[O:15])[NH:4][C:5]([N:7]([CH3:13])[CH2:8][CH2:9][CH2:10][CH:11]=[CH2:12])=[O:6].[OH-].[Li+]>O1CCCC1>[CH3:1][C:2]([CH3:19])([CH3:18])[C@@H:3]([C:14]([OH:16])=[O:15])[NH:4][C:5]([N:7]([CH3:13])[CH2:8][CH2:9][CH2:10][CH:11]=[CH2:12])=[O:6]Komponenten
4
Edukt 2
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 1
Versuchsvorschrift
A solution of methyl 3-methyl-N-{[methyl(pent-4-enyl)amino]carbonyl}-L-valinate (3.00 g, 11.2 mmol), lithium hydroxide (1M, 56.0 mL, 56.0 mmol) in tetrahydrofuran (40 mL) was heated to 50° C. for 1 h. Contents of the reaction flask were cooled and evaporated to remove tetrahydrofuran. The remaining mixture was poured into 5% potassium bisulfate and extracted with methylene chloride (3×10 mL). The combined organic extracts were dried with anhydrous sodium sulfate, filtered and evaporated to give the title compound as a colorless oil, 2.87 g (100% yield). LRMS (ESI) m/z 257 [(M+H)+; calcd for C13H25N2O3: 257].