Multi-step reaction with 9 steps
1.1: palladium on activated charcoal; hydrogen / ethanol / 24 h
2.1: diethylamino-sulfur trifluoride / dichloromethane / 1 h / -78 °C / Inert atmosphere
2.2: -78 - 20 °C
3.1: 1,8-diazabicyclo[5.4.0]undec-7-ene / dichloromethane / 0.33 h / -47 °C / Inert atmosphere
3.2: -47 - 20 °C
4.1: methoxybenzene; trifluoroacetic acid / dichloromethane / 0.5 h
5.1: O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate; N-ethyl-N,N-diisopropylamine; HATU / dichloromethane / 1.5 h / 20 °C / Inert atmosphere
6.1: dihydrogen peroxide; lithium hydroxide / methanol / 3 h / 20 °C
6.2: pH 1
7.1: methoxybenzene; trifluoroacetic acid / dichloromethane / 0.67 h
8.1: O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate; N-ethyl-N,N-diisopropylamine; HATU; 3-[(diethoxyphosphinyl)oxy]-1,2,3-benzotriazin-4(3H)-one / dichloromethane; acetonitrile / 12 h
9.1: sodium hydride / tetrahydrofuran; N,N-dimethyl-formamide / 12 h / 20 °C / Inert atmosphere
With
diethylamino-sulfur trifluoride; palladium on activated charcoal; hydrogen; dihydrogen peroxide; sodium hydride; O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate; methoxybenzene; 1,8-diazabicyclo[5.4.0]undec-7-ene; N-ethyl-N,N-diisopropylamine; HATU; trifluoroacetic acid; 3-[(diethoxyphosphinyl)oxy]-1,2,3-benzotriazin-4(3H)-one; lithium hydroxide;
In
tetrahydrofuran; methanol; ethanol; dichloromethane; N,N-dimethyl-formamide; acetonitrile;
DOI:10.1016/j.tet.2011.11.089