N-[(1S)-2-[(1S,3S,5S)-3-氰基-2-氮杂双环[3.1.0]己烷-2-基]-1-(3-羟基三环[3.3.1.13,7]癸烷-1-基)-2-氧代乙基]氨基甲酸 1,1-二甲基乙酯合成路线 (共 18 条)
反应条件
1.1: triethylamine / methanol
2.1: potassium permanganate; potassium hydroxide / 90 °C
3.1: benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine / ethyl acetate; acetonitrile / 3 h
4.1: trifluoroacetic anhydride; pyridine / tetrahydrofuran / 0.5 h / 0 °C
4.2: 18 h / 20 °C
View Scheme
参考文献
Dong, Jizhe; Gong, Yanchun; Liu, Jun; Chen, Xiangfeng; Wen, Xiaoan; Sun, Hongbin
Bioorganic and Medicinal Chemistry, 2014 , vol. 22, # 4 p. 1383 - 1393
反应条件
1.1: 4-(N,N-dimethlyamino)pyridine; trifluoroacetic anhydride; N-ethyl-N,N-diisopropylamine
2.1: water; lithium hydroxide hydrate / ethanol
3.1: ammonia; N-ethyl-N,N-diisopropylamine; methanesulfonyl chloride / tetrahydrofuran
4.1: diethylzinc / ethylene glycol dimethyl ether; dichloromethane / -30 - 20 °C
5.1: isopropyl alcohol / 60 °C
6.1: benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine / ethyl acetate; acetonitrile / 3 h
7.1: trifluoroacetic anhydride; pyridine / tetrahydrofuran / 0.5 h / 0 °C
7.2: 18 h / 20 °C
View Scheme
参考文献
Dong, Jizhe; Gong, Yanchun; Liu, Jun; Chen, Xiangfeng; Wen, Xiaoan; Sun, Hongbin
Bioorganic and Medicinal Chemistry, 2014 , vol. 22, # 4 p. 1383 - 1393
反应条件
1.1: lithium triethylborohydride / toluene / -70 - -60 °C
2.1: 4-(N,N-dimethlyamino)pyridine; trifluoroacetic anhydride; N-ethyl-N,N-diisopropylamine
3.1: water; lithium hydroxide hydrate / ethanol
4.1: ammonia; N-ethyl-N,N-diisopropylamine; methanesulfonyl chloride / tetrahydrofuran
5.1: diethylzinc / ethylene glycol dimethyl ether; dichloromethane / -30 - 20 °C
6.1: isopropyl alcohol / 60 °C
7.1: benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine / ethyl acetate; acetonitrile / 3 h
8.1: trifluoroacetic anhydride; pyridine / tetrahydrofuran / 0.5 h / 0 °C
8.2: 18 h / 20 °C
View Scheme
参考文献
Dong, Jizhe; Gong, Yanchun; Liu, Jun; Chen, Xiangfeng; Wen, Xiaoan; Sun, Hongbin
Bioorganic and Medicinal Chemistry, 2014 , vol. 22, # 4 p. 1383 - 1393
反应条件
1.1: 4-(N,N-dimethlyamino)pyridine
2.1: lithium triethylborohydride / toluene / -70 - -60 °C
3.1: 4-(N,N-dimethlyamino)pyridine; trifluoroacetic anhydride; N-ethyl-N,N-diisopropylamine
4.1: water; lithium hydroxide hydrate / ethanol
5.1: ammonia; N-ethyl-N,N-diisopropylamine; methanesulfonyl chloride / tetrahydrofuran
6.1: diethylzinc / ethylene glycol dimethyl ether; dichloromethane / -30 - 20 °C
7.1: isopropyl alcohol / 60 °C
8.1: benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine / ethyl acetate; acetonitrile / 3 h
9.1: trifluoroacetic anhydride; pyridine / tetrahydrofuran / 0.5 h / 0 °C
9.2: 18 h / 20 °C
View Scheme
参考文献
Dong, Jizhe; Gong, Yanchun; Liu, Jun; Chen, Xiangfeng; Wen, Xiaoan; Sun, Hongbin
Bioorganic and Medicinal Chemistry, 2014 , vol. 22, # 4 p. 1383 - 1393
反应条件
1.1: water; lithium hydroxide hydrate / ethanol
2.1: ammonia; N-ethyl-N,N-diisopropylamine; methanesulfonyl chloride / tetrahydrofuran
3.1: diethylzinc / ethylene glycol dimethyl ether; dichloromethane / -30 - 20 °C
4.1: isopropyl alcohol / 60 °C
5.1: benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine / ethyl acetate; acetonitrile / 3 h
6.1: trifluoroacetic anhydride; pyridine / tetrahydrofuran / 0.5 h / 0 °C
6.2: 18 h / 20 °C
View Scheme
参考文献
Dong, Jizhe; Gong, Yanchun; Liu, Jun; Chen, Xiangfeng; Wen, Xiaoan; Sun, Hongbin
Bioorganic and Medicinal Chemistry, 2014 , vol. 22, # 4 p. 1383 - 1393
反应条件
1.1: diethylzinc / ethylene glycol dimethyl ether; dichloromethane / -30 - 20 °C
2.1: isopropyl alcohol / 60 °C
3.1: benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine / ethyl acetate; acetonitrile / 3 h
4.1: trifluoroacetic anhydride; pyridine / tetrahydrofuran / 0.5 h / 0 °C
4.2: 18 h / 20 °C
View Scheme
参考文献
Dong, Jizhe; Gong, Yanchun; Liu, Jun; Chen, Xiangfeng; Wen, Xiaoan; Sun, Hongbin
Bioorganic and Medicinal Chemistry, 2014 , vol. 22, # 4 p. 1383 - 1393
反应条件
1.1: isopropyl alcohol / 60 °C
2.1: benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine / ethyl acetate; acetonitrile / 3 h
3.1: trifluoroacetic anhydride; pyridine / tetrahydrofuran / 0.5 h / 0 °C
3.2: 18 h / 20 °C
View Scheme
参考文献
Dong, Jizhe; Gong, Yanchun; Liu, Jun; Chen, Xiangfeng; Wen, Xiaoan; Sun, Hongbin
Bioorganic and Medicinal Chemistry, 2014 , vol. 22, # 4 p. 1383 - 1393
反应条件
1.1: benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine / ethyl acetate; acetonitrile / 3 h
2.1: trifluoroacetic anhydride; pyridine / tetrahydrofuran / 0.5 h / 0 °C
2.2: 18 h / 20 °C
View Scheme
参考文献
Dong, Jizhe; Gong, Yanchun; Liu, Jun; Chen, Xiangfeng; Wen, Xiaoan; Sun, Hongbin
Bioorganic and Medicinal Chemistry, 2014 , vol. 22, # 4 p. 1383 - 1393