Multi-step reaction with 8 steps
1.1: N-Bromosuccinimide; 2,2'-azobis(isobutyronitrile) / tetrachloromethane / 18 h / Inert atmosphere; Reflux
2.1: sodium azide / acetonitrile / 20.5 h / 20 °C / Inert atmosphere
3.1: hydrogen / palladium 10% on activated carbon / ethyl acetate / 18 h / 2585.81 Torr
4.1: water; lithium hydroxide / tetrahydrofuran; methanol / 3 h / 0 - 20 °C
5.1: N-ethyl-N,N-diisopropylamine; HATU / N,N-dimethyl-formamide / 0.5 h / 0 °C / Inert atmosphere
5.2: 18.08 h / 0 - 20 °C
6.1: trifluoroacetic acid / dichloromethane / 5 h / 20 °C / Inert atmosphere
7.1: triethylamine / acetonitrile / 50 h / 0 - 20 °C
8.1: di-isopropyl azodicarboxylate / tetrahydrofuran / 0.25 h / 0 °C / Inert atmosphere
8.2: 18.25 h / 0 - 20 °C / Inert atmosphere
With
N-Bromosuccinimide; sodium azide; 2,2'-azobis(isobutyronitrile); di-isopropyl azodicarboxylate; water; hydrogen; triethylamine; N-ethyl-N,N-diisopropylamine; HATU; trifluoroacetic acid; lithium hydroxide;
palladium 10% on activated carbon;
In
tetrahydrofuran; methanol; tetrachloromethane; dichloromethane; ethyl acetate; N,N-dimethyl-formamide; acetonitrile;