Multi-step reaction with 12 steps
1.1: sodium acetate / acetic acid / 20?h / 120?°C
2.1: mineral oil; N,N-dimethyl-formamide / 15?min / Cooling with ice
2.2: 1 h / Cooling with ice
3.1: triethylamine / ethanol / 18 h / 85 °C
4.1: sodium ethanolate / 1 h / 60 °C
5.1: 1,8-diazabicyclo[5.4.0]undec-7-ene / N,N-dimethyl-formamide / 0.17 h / 20 °C
5.2: 4 h / 20 °C
6.1: sodium hydroxide / tetrahydrofuran; ethanol / 18 h / 20 °C
7.1: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; benzotriazol-1-ol / N,N-dimethyl-formamide / 18 h / 20 °C
8.1: hydrogenchloride / ethyl acetate / 4 h / 20 °C
9.1: potassium carbonate / N,N-dimethyl-formamide / 16 h / 80 °C
10.1: methoxybenzene; trifluorormethanesulfonic acid; trifluoroacetic acid / 1 h / 80 °C
11.1: triethylamine / tetrahydrofuran / 4 h / 0 °C
12.1: sodium t-butanolate / N,N-dimethyl-formamide; 1,2-dimethoxyethane / 0.5 h / 0 °C
12.2: 0.17 h / 20 °C
With
hydrogenchloride; trifluorormethanesulfonic acid; sodium ethanolate; sodium acetate; potassium carbonate; benzotriazol-1-ol; methoxybenzene; 1,8-diazabicyclo[5.4.0]undec-7-ene; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; trifluoroacetic acid; sodium hydroxide; sodium t-butanolate;
In
tetrahydrofuran; 1,2-dimethoxyethane; ethanol; acetic acid; ethyl acetate; N,N-dimethyl-formamide; mineral oil;
DOI:10.1016/j.bmc.2012.07.039