Multi-step reaction with 9 steps
1.1: sodium acetate / acetic acid / 20?h / 120?°C
2.1: sodium hydride / mineral oil; N,N-dimethyl-formamide / 15?min / Cooling with ice
2.2: 1 h / Cooling with ice
3.1: triethylamine / ethanol / 12 h / 85 °C
4.1: sodium ethanolate / ethanol / 18 h / 50 °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: triethylamine / tetrahydrofuran / 15 h / 0 - 20 °C
9.1: sodium hydroxide / tetrahydrofuran; ethanol; water / 2 h / 20 °C
With
sodium ethanolate; sodium acetate; sodium hydride; benzotriazol-1-ol; 1,8-diazabicyclo[5.4.0]undec-7-ene; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; sodium hydroxide;
In
tetrahydrofuran; ethanol; water; acetic acid; N,N-dimethyl-formamide; mineral oil;
DOI:10.1016/j.bmc.2012.07.039