Lithium Hydroxide → (2S)-3-Methyl-2-({[methyl(pent-4-en-1-yl)amino]carbonyl}amino)butanoic acid

Participants

Reaction Steps

A 250 mL round bottom flask under nitrogen was charged with methyl (2S)-3-methyl-2-({[methyl(pent-4-en-1-yl)amino]carbonyl}amino)butanoate from the previous step, THF (40 mL), and aqueous LiOH (1 M, 60 mmol, 60 mL). The reaction mixture was stirred 18 hours. THF was removed by evaporation. The remaining aqueous mixture was poured into water and washed once with EtOAc. The aqueous layer was acidified with 1 M hydrochloric acid and extracted with EtOAc (3×). Combined organic extracts were dried with anhydrous NaSO4, filtered and evaporated to give the title compound as a pale oil (2.34 g, 9.66 mmol, 95%). LRMS m/e [M+H]+ 243.

Provenance & Evidence