Multi-step reaction with 13 steps
1.1: methanol; benzene; hexane / 0.5 h / Inert atmosphere
2.1: ammonium hydroxide / methanol
3.1: Lawessons reagent / 1,2-dimethoxyethane / 20 °C / Inert atmosphere
4.1: potassium hydrogencarbonate / 1,2-dimethoxyethane / 0.25 h / 20 °C / Inert atmosphere
4.2: 20 °C / Inert atmosphere
4.3: 0 - 20 °C / Inert atmosphere
5.1: trifluoroacetic acid; methoxybenzene / dichloromethane
6.1: 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
7.1: trifluoroacetic acid; methoxybenzene / dichloromethane
8.1: 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
9.1: lithium hydroxide; dihydrogen peroxide / ethanol
10.1: trifluoroacetic acid; methoxybenzene / dichloromethane
11.1: 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
12.1: hydrogen bromide; acetic acid / 1 h
13.1: N-ethyl-N,N-diisopropylamine / dichloromethane / 2 h / Inert atmosphere
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; hexane; dichloromethane; benzene;
DOI:10.1021/ol401749p