Multi-step reaction with 11 steps
1.1: ammonium hydroxide / ethanol / 4 h / 60 - 65 °C
1.3: Auto-seeded programmed polythermic preferential crystallization; Resolution of racemate
2.1: sodium hydroxide / water / 72 h / Reflux
3.1: thionyl chloride / -15 °C / Reflux
3.2: 2 h / 20 °C
4.1: HATU / dichloromethane / 0.33 h / 0 °C / Inert atmosphere
4.2: 36 h / 20 °C / Inert atmosphere
5.1: hydrogenchloride; palladium 10% on activated carbon; hydrogen / methanol; isopropyl alcohol / 8 h / 20 °C / 760.05 Torr
6.1: HATU / tetrahydrofuran / 0.17 h / 0 °C / Inert atmosphere
6.2: 6 h / 20 °C / Inert atmosphere
6.3: 18 h / 20 °C / Inert atmosphere
7.1: hydrogenchloride; palladium 10% on activated carbon; hydrogen / methanol; isopropyl alcohol / 20 °C / 760.05 Torr
8.1: HATU / tetrahydrofuran / 0.17 h / 0 °C / Inert atmosphere
8.2: 8 h / 20 °C / Inert atmosphere
8.3: 20 °C / Inert atmosphere
9.1: sodium hydroxide / water; isopropyl alcohol / 5 h / 0 - 20 °C
9.2: 0 °C / pH 4
10.1: palladium 10% on activated carbon; hydrogen / methanol / 20 °C / 760.05 Torr
11.1: (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate / N,N-dimethyl-formamide / 0.17 h / 20 °C
11.2: 48 h / 20 °C
With
hydrogenchloride; ammonium hydroxide; thionyl chloride; palladium 10% on activated carbon; hydrogen; (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate; HATU; sodium hydroxide;
In
tetrahydrofuran; methanol; ethanol; dichloromethane; water; N,N-dimethyl-formamide; isopropyl alcohol;
1.1: Bucherer-Bergs reaction;
DOI:10.1016/j.tet.2011.06.032