Multi-step reaction with 14 steps
1.1: dmap; triethylamine / dichloromethane / 20 h / Inert atmosphere; Cooling; Reflux
2.1: sulfuric acid; acetic acid / 3.5 h
3.1: N,O-bis-(trimethylsilyl)-acetamide; trimethylsilyl trifluoromethanesulfonate / acetonitrile / 1 h / 20 °C / Inert atmosphere; Reflux
4.1: methylamine / water; tetrahydrofuran / 0.5 h / 20 °C
5.1: dmap; trifluoromethane sulfonyl chloride / dichloromethane / 1 h / 20 °C / Inert atmosphere; Cooling with ice
6.1: sodium hydroxide; water / tetrahydrofuran / 1.5 h / 20 °C
7.1: pyridine / dichloromethane / 1 h / Inert atmosphere; Cooling with ice
8.1: sodium azide / N,N-dimethyl-formamide / 48 h / Inert atmosphere
9.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 12.5 h / Inert atmosphere
10.1: dipyridinium dichromate / N,N-dimethyl-formamide / 4.5 h / 20 °C / Inert atmosphere; Molecular sieve
10.2: 1 h
11.1: water; tributylphosphine / tetrahydrofuran / 3.5 h / 20 °C
12.1: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / N,N-dimethyl-formamide / 21.5 h / 20 °C / Inert atmosphere; Cooling with ice
13.1: 1,8-diazabicyclo[5.4.0]undec-7-ene / N,N-dimethyl-formamide / 0.25 h / Inert atmosphere; Cooling with ice
13.2: 0.5 h / Cooling with ice
14.1: sodium hydride / N,N-dimethyl-formamide / 0.5 h / Inert atmosphere; Cooling with acetone-dry ice
14.2: 0.5 h / 20 °C / Cooling with acetone-dry ice
With
pyridine; dmap; dipyridinium dichromate; sodium azide; N,O-bis-(trimethylsilyl)-acetamide; tributylphosphine; trifluoromethane sulfonyl chloride; trimethylsilyl trifluoromethanesulfonate; sulfuric acid; tetrabutyl ammonium fluoride; water; sodium hydride; acetic acid; 1,8-diazabicyclo[5.4.0]undec-7-ene; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; methylamine; sodium hydroxide;
In
tetrahydrofuran; dichloromethane; water; N,N-dimethyl-formamide; acetonitrile;