[1S-[1R*(R*),2R*,4R*]]-[4-[[(3-氨基-2,2-二甲基-3-氧代丙基)氨基]羰基]-2-羟基-1-[2-[[4-甲氧基-3-(3-甲氧基丙氧基)苯基]甲基]-3-甲基丁基]-5-甲基己基]-氨基甲酸叔丁酯合成路线 （共 49 条）
反应条件
1: 89 percent / DMSO; ClC(O)C(O)Cl; Et3N / CH2Cl2
2: Mg
3: 23 percent / H2 / Pd(OH)2/C
4: 38 percent / TPAP; NMMO
5: 65 percent / 2-hydroxypyridine; Et3N
View Scheme
参考文献
Dong, Hua; Zhang, Zhi-Liu; Huang, Jia-Hui; Ma, Rujian; Chen, Shu-Hui; Li, Ge
Tetrahedron Letters, 2005 , vol. 46, # 37 p. 6337 - 6340
反应条件
1: NaBH4 / ethanol
2: 89 percent / DMSO; ClC(O)C(O)Cl; Et3N / CH2Cl2
3: Mg
4: 23 percent / H2 / Pd(OH)2/C
5: 38 percent / TPAP; NMMO
6: 65 percent / 2-hydroxypyridine; Et3N
View Scheme
参考文献
Dong, Hua; Zhang, Zhi-Liu; Huang, Jia-Hui; Ma, Rujian; Chen, Shu-Hui; Li, Ge
Tetrahedron Letters, 2005 , vol. 46, # 37 p. 6337 - 6340
反应条件
1: 81 percent / LiOH; H2O2
2: 95 percent / LAH / tetrahydrofuran
3: 97 percent / PPh3; NBS / CH2Cl2
4: 68 percent / n-BuLi
5: HCl / acetonitrile
6: Et3N
7: NaBH4 / ethanol
8: 89 percent / DMSO; ClC(O)C(O)Cl; Et3N / CH2Cl2
9: Mg
10: 23 percent / H2 / Pd(OH)2/C
11: 38 percent / TPAP; NMMO
12: 65 percent / 2-hydroxypyridine; Et3N
View Scheme
参考文献
Dong, Hua; Zhang, Zhi-Liu; Huang, Jia-Hui; Ma, Rujian; Chen, Shu-Hui; Li, Ge
Tetrahedron Letters, 2005 , vol. 46, # 37 p. 6337 - 6340
反应条件
1.1: iodine; magnesium; .alpha.-butylene bromide / tetrahydrofuran / 1 h / Inert atmosphere; Reflux
1.2: 2 h / -78 °C
1.3: -78 °C
2.1: hydrogenchloride; hydrogen; acetic acid / platinum(IV) oxide / water / 3 h / 20 °C / 760.05 Torr
3.1: sodium hydroxide; water / ethanol / 3 h / 50 °C
4.1: triethylamine; 2-hydroxy-pyridine / tert-butyl methyl ether / 18 h / 80 °C
View Scheme
参考文献
CarboDesign LLC
Patent: US2011/92706 A1, 2011 ;
反应条件
1.1: iodine; magnesium; .alpha.-butylene bromide / tetrahydrofuran / 1 h / Inert atmosphere; Reflux
1.2: 2 h / -78 °C
1.3: -78 °C
2.1: hydrogenchloride; hydrogen; acetic acid / platinum(IV) oxide / water / 3 h / 20 °C / 760.05 Torr
3.1: sodium hydroxide; water / ethanol / 3 h / 50 °C
4.1: triethylamine; 2-hydroxy-pyridine / tert-butyl methyl ether / 18 h / 80 °C
View Scheme
参考文献
CarboDesign LLC
Patent: US2011/92706 A1, 2011 ;
反应条件
1: hydrogenchloride; hydrogen; acetic acid / platinum(IV) oxide / water / 3 h / 20 °C / 760.05 Torr
2: sodium hydroxide; water / ethanol / 3 h / 50 °C
3: triethylamine; 2-hydroxy-pyridine / tert-butyl methyl ether / 18 h / 80 °C
View Scheme
参考文献
CarboDesign LLC
Patent: US2011/92706 A1, 2011 ;
反应条件
1.1: diisopropylamine; n-butyllithium / hexane; tetrahydrofuran / 0.5 h / -40 °C / Inert atmosphere
1.2: 3 h / -40 - -10 °C / Inert atmosphere
2.1: iodine; magnesium; .alpha.-butylene bromide / tetrahydrofuran / 1 h / Reflux; Inert atmosphere
2.2: 6 h / -78 - -35 °C / Inert atmosphere
2.3: -35 °C / Inert atmosphere
3.1: hydrogenchloride; hydrogen; acetic acid / palladium 10 on activated carbon / water / 3 h / 20 °C / 760.05 Torr
4.1: 4-(N,N-dimethlyamino)pyridine; triethylamine / tetrahydrofuran / 24 h / 20 °C
5.1: triethylamine; 2-hydroxy-pyridine / tert-butyl methyl ether / 18 h / 80 °C
View Scheme
参考文献
CarboDesign LLC
Patent: US2011/105767 A1, 2011 ;
反应条件
1.1: iodine; magnesium; .alpha.-butylene bromide / tetrahydrofuran / 1 h / Reflux; Inert atmosphere
1.2: 6 h / -78 - -35 °C / Inert atmosphere
1.3: -35 °C / Inert atmosphere
2.1: hydrogenchloride; hydrogen; acetic acid / palladium 10 on activated carbon / water / 3 h / 20 °C / 760.05 Torr
3.1: 4-(N,N-dimethlyamino)pyridine; triethylamine / tetrahydrofuran / 24 h / 20 °C
4.1: triethylamine; 2-hydroxy-pyridine / tert-butyl methyl ether / 18 h / 80 °C
View Scheme
参考文献
CarboDesign LLC
Patent: US2011/105767 A1, 2011 ;
反应条件
1: hydrogenchloride; hydrogen; acetic acid / palladium 10 on activated carbon / water / 3 h / 20 °C / 760.05 Torr
2: 4-(N,N-dimethlyamino)pyridine; triethylamine / tetrahydrofuran / 24 h / 20 °C
3: triethylamine; 2-hydroxy-pyridine / tert-butyl methyl ether / 18 h / 80 °C
View Scheme
参考文献
CarboDesign LLC
Patent: US2011/105767 A1, 2011 ;
反应条件
1.1: thionyl chloride / dichloromethane / 3 h / 20 °C / Inert atmosphere
2.1: n-butyllithium; n-butyl-magnesium bromide / hexane; tetrahydrofuran / 0 °C
2.2: 5 h / -78 °C / Inert atmosphere
3.1: 4-(N,N-dimethlyamino)pyridine; triethylamine; hydrogen / palladium 10 on activated carbon / tetrahydrofuran / 24 h / 20 °C
4.1: triethylamine; 2-hydroxy-pyridine / tert-butyl methyl ether / 18 h / 80 °C
View Scheme
参考文献
CarboDesign LLC
Patent: US2011/137047 A1, 2011 ;
