Multi-step reaction with 12 steps
1.1: 56 percent / 1-(3-(dimethylamino)propyl)-3-ethylcarbodiimide*HCl; 1-hydroxybenzotriazole; 4-methylmorpholine / CH2Cl2 / 24 h / 0 - 20 °C
2.1: 81 percent / H2 / Pd(OH)2/C / methanol; tetrahydrofuran / 20 °C
3.1: (diethylamino)sulfur trifluoride / CH2Cl2 / 1.5 h / -78 °C
3.2: 57 percent / BrCCl3; DBU / CH2Cl2 / 24 h / 0 - 20 °C
4.1: 88 percent / aq. NaOH / tetrahydrofuran / 24 h / 20 °C
5.1: 87 percent / 1-(3-(dimethylamino)propyl)-3-ethylcarbodiimide*HCl; 1-hydroxybenzotriazole; 4-methylmorpholine / CH2Cl2 / 24 h / 0 - 20 °C
6.1: 50 percent / Lawesson's reagent / tetrahydrofuran / 18 h / Heating
7.1: 91 percent / HCl / dioxane / 24 h / 20 °C
8.1: 82 percent / 1-(3-(dimethylamino)propyl)-3-ethylcarbodiimide*HCl; 1-hydroxybenzotriazole; 4-methylmorpholine / CH2Cl2 / 48 h / 0 - 20 °C
9.1: aq. NaOH / tetrahydrofuran / 24 h / 20 °C
10.1: HCl / dioxane / 18 h / 20 °C
11.1: 75 percent / O-(7-azabenzotriazol-1-yl)-N,N,N',N'-tetramethyluronium*PF6; 4-methylmorpholine / CH2Cl2; dimethylformamide / 72 h / 0 - 20 °C
12.1: 89 percent / (diethylamino)sulfur trifluoride / CH2Cl2 / 2 h / -78 °C
With
Lawessons reagent; 4-methyl-morpholine; hydrogenchloride; sodium hydroxide; diethylamino-sulfur trifluoride; hydrogen; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; HATU;
palladium dihydroxide;
In
tetrahydrofuran; 1,4-dioxane; methanol; dichloromethane; N,N-dimethyl-formamide;
DOI:10.1039/b416530f