Multi-step reaction with 22 steps
1: 88.7 percent / Et3N / tetrahydrofuran / 1 h / Ambient temperature
2: KOH / ethanol / 19 h / Ambient temperature
3: 1 N aq. NaOH / 0.33 h / 90 °C
4: 85 percent / BSA / CH2Cl2 / 5 h / 0 - 20 °C
5: 32.1 percent / diethyl ether; ethyl acetate / 0.17 h
6: 93.6 percent / Et3N, DMAP / CH2Cl2 / 16 h / Ambient temperature
7: 72.1 percent / thiophenol, TFA / CH2Cl2 / 0.5 h / 0 °C
8: 49.1 percent / 2-ethoxy-N-ethoxycarbonyl-1,2-dihydroquinoline / CH2Cl2 / 14 h / Ambient temperature
9: DBU / toluene / 2.5 h / Ambient temperature
10: 98 percent / imidazole / dimethylformamide / 16 h / Ambient temperature
11: 87.3 percent / NaOH / methanol / 48 h / 30 °C
12: 32.6 percent / Et3N, EEDQ / CH2Cl2 / 33 h / Ambient temperature
13: 21.2 percent / acetone; toluene / 1.5 h / 0 °C / Irradiation
14: 99.9 percent / 67percent AcOH / 28 h / 25 °C
15: 86.5 percent / EDC*HCl, DMAP / CH2Cl2 / 12 h / Ambient temperature
16: 4 N HCl, anisole / dioxane / 0.5 h / Ambient temperature
17: Et3N, HOBT, EDC*HCl / CH2Cl2 / 1 h / Ambient temperature
18: 4 N HCl, anisole / dioxane / 0.5 h / Ambient temperature
19: Et3N, HOBT, EDC*HCl / CH2Cl2 / 8 h / Ambient temperature
20: 82.6 percent / Zn, 90percent AcOH / Ambient temperature
21: EDC*HCl / CH2Cl2; dimethylformamide / Ambient temperature
22: TFA, anisole / 0.5 h / Ambient temperature
With
1H-imidazole; hydrogenchloride; benzenesulfonamide; dmap; potassium hydroxide; sodium hydroxide; benzotriazol-1-ol; acetic acid; thiophenol; methoxybenzene; 1,8-diazabicyclo[5.4.0]undec-7-ene; N-ethoxycarbonyl-2-ethoxy-1,2-dihydroquinoline; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; trifluoroacetic acid; zinc;
In
tetrahydrofuran; 1,4-dioxane; methanol; diethyl ether; ethanol; dichloromethane; ethyl acetate; N,N-dimethyl-formamide; acetone; toluene;
DOI:10.1248/cpb.45.236