Multi-step reaction with 10 steps
1.1: methanol / 2 h / Cooling with water bath
2.1: -4 - 20 °C
3.1: hydrogen / palladium 10% on activated carbon / methanol / 60 h / 20 °C / 760.05 Torr / Inert atmosphere
4.1: dmap; pyridine / dichloromethane / 14.08 h / 20 °C
5.1: sodium hydride / N,N-dimethyl-formamide / 1 h / 20 °C / Cooling with ice
5.2: 3 h / 20 °C / Cooling with ice
6.1: sodium hydroxide; water / tetrahydrofuran / 48 h / 60 °C
6.2: pH 2
7.1: triethylamine; diphenyl phosphoryl azide / 1,4-dioxane / 4 h / 20 °C / Inert atmosphere; Reflux
7.2: 2 h / Reflux
8.1: triethylamine / chloroform / 3.5 h / 60 °C
9.1: ammonia / 1,4-dioxane / 0.33 h / 120 °C / Microwave irradiation
10.1: trifluoroacetic acid / dichloromethane / 0.5 h / 20 °C
With
pyridine; methanol; dmap; diphenyl phosphoryl azide; ammonia; water; hydrogen; sodium hydride; triethylamine; trifluoroacetic acid; sodium hydroxide;
palladium 10% on activated carbon;
In
tetrahydrofuran; 1,4-dioxane; methanol; dichloromethane; chloroform; N,N-dimethyl-formamide;