Multi-step reaction with 8 steps
1: 1.) NaOEt, 2.) KI / 1.) EtOH, reflux, 30 min, 2.) DMF, EtOH, 55 deg C, 24 h
2: 1.) 6 N aq. NaOH / 1.) EtOH, RT, 24 h, 2.) toluene, reflux, 3 h
3: 94 percent / 6 N aq. HCl / 4.5 h / Heating
4: Et3N / dioxane; H2O / Ambient temperature
5: toluene / 3 h / 95 °C
6: K2CO3 / dimethylformamide / 48 h / Ambient temperature
7: HCl gas / CH2Cl2 / 4 h / Ambient temperature
8: 1-hydroxybenzotriazole, 4-methylmorpholine, N-<(dimethylamino)propyl>-N'-ethylcarbodiimide*HCl / CH2Cl2
With
4-methyl-morpholine; hydrogenchloride; sodium hydroxide; sodium ethanolate; potassium carbonate; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; potassium iodide;
In
1,4-dioxane; dichloromethane; water; N,N-dimethyl-formamide; toluene;
DOI:10.1021/jm960871c