Triethylamine → (3R,4R,5S)-1-(3-(bis(tert-butoxycarbonyl)amino)pyridin-4-yl)-3-((tert-butoxycarbonyl)amino)-5-methylpiperidin-4-yl methanesulfonate

Participants

Reaction Steps

To a solution of di-tert-butyl (4-{(3R,4R,5S)-3-[(tert-butoxycarbonyl)amino]-4-hydroxy-5-methylpiperidin-1-yl}pyridin-3-yl)imidodicarbonate (500 mg, 0.957 mmol) in DCM (4.5 mL), triethylamine (0.227 mL, 1.63 mmol) was added followed by methanesulfonyl chloride (0.096 mL, 1.24 mmol). The capped solution was stirred at room temperature for 1 h. The reaction mixture was quenched with aq. NaHCO3, extracted with EtOAc. The organic layer was washed with brine, dried, filtered and concentrated under reduced pressure to give the sub-title compound as a light yellow powder (574 mg, 100%). LCMS calc. for C27H45N4O9S (M+H)+: m/z=601.3. Found: 601.2.

Provenance & Evidence