Multi-step reaction with 10 steps
1: 20percent aq. NaOH / toluene / 24 h
2: SOCl2 / CH2Cl2 / 16 h / Ambient temperature
3: 88 percent / aq. H2SO4 / H2O / 16 h / Heating
4: 97 percent / 1-hydroxybenzotriazole hydrate, dimethyl-3-<3-(dimethylamino)propyl>carbodiimide hydrochloride, triethylamine / dimethylformamide / 16 h
5: 40 percent / trifluoroacetic acid / CHCl3 / 2.5 h
6: 93 percent / 20percent aq. NaOH / ethanol / 16 h / Heating
7: 66 percent / 1-hydroxybenzotriazole hydrate, dimethyl-3-<3-(dimethylamino)propyl>carbodiimide hydrochloride, N-methylmorpholine / dimethylformamide / 17 h
8: 8.5 g / tetra-n-butylammonium fluoride / tetrahydrofuran / 20 h
9: 98 percent / H2 / 10percent Pd/C / tetrahydrofuran; methanol / 96 h
10: 75 percent / Cs2CO3 / dioxane / 1 h / 80 °C
With
4-methyl-morpholine; sodium hydroxide; thionyl chloride; dimethyl-3-<3-(dimethylamino)propyl>carbodiimide hydrochloride; sulfuric acid; tetrabutyl ammonium fluoride; hydrogen; caesium carbonate; 1-hydroxybenzotriazol-hydrate; triethylamine; trifluoroacetic acid;
palladium on activated charcoal;
In
tetrahydrofuran; 1,4-dioxane; methanol; ethanol; dichloromethane; chloroform; water; N,N-dimethyl-formamide; toluene;
DOI:10.1021/jm00088a003