Multi-step reaction with 7 steps
1: 100 percent / 1.0 M aq. NaOH / dioxane / 18 h / 0 °C
2: 1.) LDA, 2.) 1,1'-carbonyldiimidazole / 1.) THF, hexane, -78 deg C, 10 min, 2.) THF, hexane, -78 deg C, 1 h
3: 1.) NaH / 1.) THF, 0 deg C, 10 min, 2.) THF, CH2Cl2, 23 deg C, 24 h
4: TFA / CH2Cl2 / 24 h / 23 °C
5: 70 percent / H2 / 10 percent Pd/C / methanol / 23 °C
6: 99 percent / 2.0 M NaOH / methanol / 2 h / 0 °C
7: 70 percent / 4-methymorpholine, 1-hydroxybenzotriazole hydrate, 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride / CH2Cl2 / 23 °C
With
4-methyl-morpholine; sodium hydroxide; hydrogen; sodium hydride; 1-hydroxybenzotriazol-hydrate; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; 1,1'-carbonyldiimidazole; trifluoroacetic acid; lithium diisopropyl amide;
palladium on activated charcoal;
In
1,4-dioxane; methanol; dichloromethane;
DOI:10.1021/jm980537b