Multi-step reaction with 11 steps
1.1: oxalyl dichloride / dichloromethane; N,N-dimethyl-formamide / 0.5 h / 20 °C
2.1: sodium hydroxide / water; tetrahydrofuran / 1 h / 20 °C
3.1: potassium hydroxide / ethanol; water / 3 h / 80 °C
3.2: 0 °C / pH 7
4.1: sodium carbonate / tetrakis(triphenylphosphine) palladium(0) / toluene; ethanol; water / 10 h / 90 °C / Inert atmosphere
4.2: pH 10
5.1: hydrogenchloride / dichloromethane; 1,4-dioxane / 0 °C
6.1: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; benzotriazol-1-ol / acetonitrile / 1 h / 10 °C
6.2: 48 h / 0 - 10 °C
7.1: triethylamine; hydrogen / 10 wt% Pd(OH)2 on carbon / methanol / 3 h / 10 °C
8.1: hydrogenchloride / dichloromethane; 1,4-dioxane / 1 h / 0 - 10 °C
9.1: N-ethyl-N,N-diisopropylamine; 2,4,6-tripropyl-1,3,5,2,4,6-trioxatriphosphinane-2,4,6-trioxide / N,N-dimethyl-formamide / 1 h / 10 °C
10.1: hydrogenchloride / dichloromethane; 1,4-dioxane / 2 h / 0 °C
11.1: sodium hydrogencarbonate / water; tetrahydrofuran / 1 h / 10 °C
With
hydrogenchloride; oxalyl dichloride; hydrogen; sodium hydrogencarbonate; sodium carbonate; benzotriazol-1-ol; 2,4,6-tripropyl-1,3,5,2,4,6-trioxatriphosphinane-2,4,6-trioxide; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; N-ethyl-N,N-diisopropylamine; potassium hydroxide; sodium hydroxide;
tetrakis(triphenylphosphine) palladium(0); 10 wt% Pd(OH)2 on carbon;
In
tetrahydrofuran; 1,4-dioxane; methanol; ethanol; dichloromethane; water; N,N-dimethyl-formamide; toluene; acetonitrile;