[1(1S,2R),5(S)]-2,3,5-三脱氧-N-(2,3-二氢-2-羟基-1H-茚-1-基)-5-[2-[(叔丁基氨基)甲酰]-1-哌嗪基]-2-(苯基甲基)-D-赤式-戊酰胺合成路线 （共 25 条）
反应条件
hydrogenchloride in isopropyl alcohol 6 h; Ambient temperature;
参考文献
Dorsey; Levin; McDaniel; Vacca; Guare; Darke; Zugay; Emini; Schleif; Quintero; Lin; Chen -; Holloway; Fitzgerald; Axel; Ostovic; Anderson; Huff
Journal of Medicinal Chemistry, 1994 , vol. 37, # 21 p. 3443 - 3451
反应条件
1: 40percent NaOH / dioxane; H2O / 14 h 2: 85 percent / 1-ethyl-3-<3-(dimethylamino)propyl>carbodiimide hydrochloride, HOBt, Et3N / dimethylformamide / 18 h 3: 96 percent / H2 / 10percent Pd/C / methanol / 3 h 4: 83 percent / (i-Pr)2NEt / propan-2-ol / 3.5 h 5: aq. LiOH / 1,2-dimethoxy-ethane / 0.5 h 6: imidazole / 1,2-dimethoxy-ethane / 20 h / 0 - 20 °C 7: 92 percent / 1-ethyl-3-<3-(dimethylamino)propyl>carbodiimide hydrochloride, HOBt, Et3N / dimethylformamide / 18 h / 0 - 20 °C 8: 69 percent / 8N HCl / propan-2-ol / 6 h / Ambient temperature View Scheme
参考文献
Journal of Medicinal Chemistry, , vol. 37, # 21 p. 3443 - 3451
反应条件
1: 85 percent / 1-ethyl-3-<3-(dimethylamino)propyl>carbodiimide hydrochloride, HOBt, Et3N / dimethylformamide / 18 h 2: 96 percent / H2 / 10percent Pd/C / methanol / 3 h 3: 83 percent / (i-Pr)2NEt / propan-2-ol / 3.5 h 4: aq. LiOH / 1,2-dimethoxy-ethane / 0.5 h 5: imidazole / 1,2-dimethoxy-ethane / 20 h / 0 - 20 °C 6: 92 percent / 1-ethyl-3-<3-(dimethylamino)propyl>carbodiimide hydrochloride, HOBt, Et3N / dimethylformamide / 18 h / 0 - 20 °C 7: 69 percent / 8N HCl / propan-2-ol / 6 h / Ambient temperature View Scheme
参考文献
Journal of Medicinal Chemistry, , vol. 37, # 21 p. 3443 - 3451
反应条件
1: 96 percent / H2 / 10percent Pd/C / methanol / 3 h 2: 83 percent / (i-Pr)2NEt / propan-2-ol / 3.5 h 3: aq. LiOH / 1,2-dimethoxy-ethane / 0.5 h 4: imidazole / 1,2-dimethoxy-ethane / 20 h / 0 - 20 °C 5: 92 percent / 1-ethyl-3-<3-(dimethylamino)propyl>carbodiimide hydrochloride, HOBt, Et3N / dimethylformamide / 18 h / 0 - 20 °C 6: 69 percent / 8N HCl / propan-2-ol / 6 h / Ambient temperature View Scheme
参考文献
Journal of Medicinal Chemistry, , vol. 37, # 21 p. 3443 - 3451
反应条件
1: 83 percent / (i-Pr)2NEt / propan-2-ol / 3.5 h 2: aq. LiOH / 1,2-dimethoxy-ethane / 0.5 h 3: imidazole / 1,2-dimethoxy-ethane / 20 h / 0 - 20 °C 4: 92 percent / 1-ethyl-3-<3-(dimethylamino)propyl>carbodiimide hydrochloride, HOBt, Et3N / dimethylformamide / 18 h / 0 - 20 °C 5: 69 percent / 8N HCl / propan-2-ol / 6 h / Ambient temperature View Scheme
参考文献
Journal of Medicinal Chemistry, , vol. 37, # 21 p. 3443 - 3451
反应条件
1: 1.) LDA / 1.) THF, hexane, 30 min, 2.) THF, hexane, 3 h 2: 97 percent / 49percent aq. HF / acetonitrile / 18 h / Ambient temperature 3: 96 percent / 2,6-lutidine / CH2Cl2 / 1.5 h / 0 °C 4: 83 percent / (i-Pr)2NEt / propan-2-ol / 3.5 h 5: aq. LiOH / 1,2-dimethoxy-ethane / 0.5 h 6: imidazole / 1,2-dimethoxy-ethane / 20 h / 0 - 20 °C 7: 92 percent / 1-ethyl-3-<3-(dimethylamino)propyl>carbodiimide hydrochloride, HOBt, Et3N / dimethylformamide / 18 h / 0 - 20 °C 8: 69 percent / 8N HCl / propan-2-ol / 6 h / Ambient temperature View Scheme
参考文献
Journal of Medicinal Chemistry, , vol. 37, # 21 p. 3443 - 3451
反应条件
1: 96 percent / imidazole / CH2Cl2 / 4 h / 0 - 20 °C 2: 1.) LDA / 1.) THF, hexane, 30 min, 2.) THF, hexane, 3 h 3: 97 percent / 49percent aq. HF / acetonitrile / 18 h / Ambient temperature 4: 96 percent / 2,6-lutidine / CH2Cl2 / 1.5 h / 0 °C 5: 83 percent / (i-Pr)2NEt / propan-2-ol / 3.5 h 6: aq. LiOH / 1,2-dimethoxy-ethane / 0.5 h 7: imidazole / 1,2-dimethoxy-ethane / 20 h / 0 - 20 °C 8: 92 percent / 1-ethyl-3-<3-(dimethylamino)propyl>carbodiimide hydrochloride, HOBt, Et3N / dimethylformamide / 18 h / 0 - 20 °C 9: 69 percent / 8N HCl / propan-2-ol / 6 h / Ambient temperature View Scheme
参考文献
Journal of Medicinal Chemistry, , vol. 37, # 21 p. 3443 - 3451
反应条件
1: 96 percent / 2,6-lutidine / CH2Cl2 / 1.5 h / 0 °C 2: 83 percent / (i-Pr)2NEt / propan-2-ol / 3.5 h 3: aq. LiOH / 1,2-dimethoxy-ethane / 0.5 h 4: imidazole / 1,2-dimethoxy-ethane / 20 h / 0 - 20 °C 5: 92 percent / 1-ethyl-3-<3-(dimethylamino)propyl>carbodiimide hydrochloride, HOBt, Et3N / dimethylformamide / 18 h / 0 - 20 °C 6: 69 percent / 8N HCl / propan-2-ol / 6 h / Ambient temperature View Scheme
参考文献
Journal of Medicinal Chemistry, , vol. 37, # 21 p. 3443 - 3451
反应条件
1: 97 percent / 49percent aq. HF / acetonitrile / 18 h / Ambient temperature 2: 96 percent / 2,6-lutidine / CH2Cl2 / 1.5 h / 0 °C 3: 83 percent / (i-Pr)2NEt / propan-2-ol / 3.5 h 4: aq. LiOH / 1,2-dimethoxy-ethane / 0.5 h 5: imidazole / 1,2-dimethoxy-ethane / 20 h / 0 - 20 °C 6: 92 percent / 1-ethyl-3-<3-(dimethylamino)propyl>carbodiimide hydrochloride, HOBt, Et3N / dimethylformamide / 18 h / 0 - 20 °C 7: 69 percent / 8N HCl / propan-2-ol / 6 h / Ambient temperature View Scheme
参考文献
Journal of Medicinal Chemistry, , vol. 37, # 21 p. 3443 - 3451
反应条件
1: 83 percent / (i-Pr)2NEt / propan-2-ol / 3.5 h 2: aq. LiOH / 1,2-dimethoxy-ethane / 0.5 h 3: imidazole / 1,2-dimethoxy-ethane / 20 h / 0 - 20 °C 4: 92 percent / 1-ethyl-3-<3-(dimethylamino)propyl>carbodiimide hydrochloride, HOBt, Et3N / dimethylformamide / 18 h / 0 - 20 °C 5: 69 percent / 8N HCl / propan-2-ol / 6 h / Ambient temperature View Scheme
参考文献
Journal of Medicinal Chemistry, , vol. 37, # 21 p. 3443 - 3451
