Multi-step reaction with 11 steps
1.1: ammonium hydroxide / methanol
2.1: Lawessons reagent / 1,2-dimethoxyethane / 20 °C / Inert atmosphere
3.1: potassium hydrogencarbonate / 1,2-dimethoxyethane / 0.25 h / 20 °C / Inert atmosphere
3.2: 20 °C / Inert atmosphere
3.3: 0 - 20 °C / Inert atmosphere
4.1: trifluoroacetic acid; methoxybenzene / dichloromethane
5.1: N-ethyl-N,N-diisopropylamine; HATU; O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate; 4-(4,6-dimethoxy-1,3,5-triazin-2-yl)-4-methylmorpholin-4-ium / dichloromethane / 1 h / 20 °C / Inert atmosphere
6.1: trifluoroacetic acid; methoxybenzene / dichloromethane
7.1: N-ethyl-N,N-diisopropylamine; HATU; 4-(4,6-dimethoxy-1,3,5-triazin-2-yl)-4-methylmorpholin-4-ium; 2,4,6-tripropyl-1,3,5,2,4,6-trioxatriphosphinane-2,4,6-trioxide / dichloromethane / 1 h / 20 °C / Inert atmosphere
8.1: lithium hydroxide; dihydrogen peroxide / ethanol
9.1: trifluoroacetic acid; methoxybenzene / dichloromethane
10.1: N-ethyl-N,N-diisopropylamine; HATU; 4-(4,6-dimethoxy-1,3,5-triazin-2-yl)-4-methylmorpholin-4-ium; 2,4,6-tripropyl-1,3,5,2,4,6-trioxatriphosphinane-2,4,6-trioxide / dichloromethane / 1 h / 20 °C / Inert atmosphere
11.1: hydrogen bromide; acetic acid / 1 h
With
Lawessons reagent; ammonium hydroxide; hydrogen bromide; dihydrogen peroxide; 4-(4,6-dimethoxy-1,3,5-triazin-2-yl)-4-methylmorpholin-4-ium; potassium hydrogencarbonate; O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate; acetic acid; methoxybenzene; 2,4,6-tripropyl-1,3,5,2,4,6-trioxatriphosphinane-2,4,6-trioxide; N-ethyl-N,N-diisopropylamine; HATU; trifluoroacetic acid; lithium hydroxide;
In
methanol; 1,2-dimethoxyethane; ethanol; dichloromethane;
DOI:10.1021/ol401749p