Multi-step reaction with 10 steps
1.1: lithium hexamethyldisilazane / tetrahydrofuran / 0.33 h / -75 - -50 °C
1.2: 0.5 h / 20 - 60 °C
2.1: potassium carbonate / N,N-dimethyl-formamide / 0.5 h / 60 °C
2.2: 60 °C
3.1: sodium hydroxide / tetrahydrofuran; ethanol / 2 h / 50 °C
4.1: benzotriazol-1-ol; N-ethyl-N,N-diisopropylamine / 2-methyltetrahydrofuran / 0.17 h / Large scale
4.2: Large scale
5.1: pyridine / toluene / 4.5 h / Reflux; Large scale
6.1: sodium carbonate / toluene; dichloromethane; water; ethyl acetate / 1 h / 20 °C / Large scale
7.1: N-ethyl-N,N-diisopropylamine; 2,6-dimethylpyridine / dichloromethane / -7 - 0 °C / Large scale
8.1: N-ethyl-N,N-diisopropylamine / dichloromethane / Large scale
9.1: tetrahydrofuran / 20 °C / Reflux; Resolution of racemate; Large scale
10.1: sodium carbonate / water; ethyl acetate / 2 h / Large scale
With
pyridine; 2,6-dimethylpyridine; sodium carbonate; potassium carbonate; benzotriazol-1-ol; N-ethyl-N,N-diisopropylamine; sodium hydroxide; lithium hexamethyldisilazane;
In
tetrahydrofuran; 2-methyltetrahydrofuran; ethanol; dichloromethane; water; ethyl acetate; N,N-dimethyl-formamide; toluene;
DOI:10.1021/op300294g