Hydrazine → (S)-N-((S)-3-amino-4-fluorobutyl)-N-((R)-1-(5-benzyl-2-(2,5-difluorophenyl)thiazol-4-yl)-2,2-dimethylpropyl)-2-hydroxypropanamide

Participants

Reaction Conditions

Reaction Steps

To a solution of (R)-1-(((R)-1-(5-benzyl-2-(2,5-difluorophenyl)thiazol-4-yl)-2,2-dimethylpropyl)((S)-3-(1,3-dioxoisoindolin-2-yl)-4-fluorobutyl)amino)-1-oxopropan-2-yl acetate (10 mg, 0.014 mmol) in EtOH (1 mL) was added anhydrous hydrazine (45 μL). The reaction was heated at 60° C. for 14 h. After cooled the reaction mixture, the white precipitate was filtered through Celite® pad with EtOH washes. The filtrate was concentrated and purified by preparative reverse phase HPLC. The pure fractions were combined and lyophilized to yield (S)-N-((S)-3-amino-4-fluorobutyl)-N-((R)-1-(5-benzyl-2-(2,5-difluorophenyl)thiazol-4-yl)-2,2-dimethylpropyl)-2-hydroxypropanamide (2.3 mg, 25%) as TFA salt. LC/MS (uplc) MH+ 543.2, 1.05 min.

Provenance & Evidence