Triethylamine → HCID 47451638, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of (S)-2-(tert-butoxycarbonylamino)-3-methylbutanoic acid (5.86 g, 27.0 mmol) in DCM (100 mL) at 0° C. was added portion wise di(1H-imidazol-1-yl)methanone (4.81 g, 29.7 mmol). Cold bath was removed and the reaction was stirred at 20° C. for 30 minutes. O,N-dimethylhydroxylamine hydrochloride (3.16 g, 32.4 mmol) was then added and followed by slow addition of triethylamine (3.28 g, 32.4 mmol). The reaction mixture was stirred at 20° C. for overnight (18 hr), and diluted with DCM (200 mL) and washed with HCl (1 M, 2×50 mL) and saturated NaHCO3 solution (2×50 mL), H2O (50 mL) and brine (50 mL). The organic was then dried (Na2SO4) and concentrated under reduced pressure to give crude product (6.61 g). LCMS m/z 261.2 (M+H)+, Rt 0.77 min.

Provenance & Evidence