Multi-step reaction with 11 steps
1.1: ammonium hydroxide / methanol; water / 20 °C / Inert atmosphere
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
4.1: pyridine / 1,2-dimethoxyethane / 0.25 h / 0 °C / Inert atmosphere
4.2: 3 h / 0 °C / Inert atmosphere
4.3: 20 °C / Inert atmosphere
5.1: trifluoroacetic acid; methoxybenzene / dichloromethane / 20 °C / Inert atmosphere
6.1: O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate; N-ethyl-N,N-diisopropylamine; HATU / dichloromethane / 1 h / 20 °C / Inert atmosphere
7.1: trifluoroacetic acid; methoxybenzene / dichloromethane / 20 °C / Inert atmosphere
8.1: O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate; N-ethyl-N,N-diisopropylamine; HATU / dichloromethane / 1 h / 20 °C / Inert atmosphere
9.1: lithium hydroxide / ethanol / Inert atmosphere
10.1: trifluoroacetic acid; methoxybenzene / dichloromethane / 1 h / 20 °C / Inert atmosphere
11.1: O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate; N-ethyl-N,N-diisopropylamine; HATU; 4-(4,6-dimethoxy-1,3,5-triazin-2-yl)-4-methylmorpholinium chloride / dichloromethane / Inert atmosphere
With
Lawessons reagent; pyridine; ammonium hydroxide; potassium hydrogencarbonate; O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate; methoxybenzene; N-ethyl-N,N-diisopropylamine; HATU; trifluoroacetic acid; 4-(4,6-dimethoxy-1,3,5-triazin-2-yl)-4-methylmorpholinium chloride; lithium hydroxide;
In
methanol; 1,2-dimethoxyethane; ethanol; dichloromethane; water;
DOI:10.1021/jo3017499