tert-Butyldimethylsilyl trifluoromethanesulphonate → Tert-butyl (2-((8-(1-((tert-butyldimethylsilyl)oxy)vinyl)-3-methylquinoxalin-2-yl)amino)-2-methylpropyl)carbamate

Participants

Reaction Steps

A solution of tert-butyl (2-((8-acetyl-3-methylquinoxalin-2-yl)amino)-2-methylpropyl)carbamate (339a, 0.78 g, 2.094 mmol), tert-butyldimethylsilyl trifluoromethanesulfonate (0.72 mL, 3.14 mmol), and TEA (0.88 mL, 6.28 mmol) in DCM (21 mL) was stirred at 0° C. for 20 min when the silyl enol ether was observed via lcms. The reaction mixture was diluted with DCM (100 mL), added to a separatory funnel, and washed with saturated aq. NaHCO3 (100 mL) before the organic layer was separated, dried over Na2SO4, and concentrated to give tert-butyl (2-((8-(1-((tert-butyldimethylsilyl)oxy)vinyl)-3-methylquinoxalin-2-yl)amino)-2-methylpropyl)carbamate (339b) as a yellow oil. MS (ESI, pos. ion) m/z: 487.3 (M+1).

Provenance & Evidence