[(1S,3S)-3-[[4-甲氧基-3-(3-甲氧基丙氧基)苯基]甲基]-4-甲基-1-[(2S,4S)-四氢-4-异丙基-5-氧代-2-呋喃基]戊基]-氨基甲酸叔丁酯合成路线 (共 84 条)
反应条件
1.1: sodium iodide / acetonitrile / Inert atmosphere; Reflux
2.1: N,N-dimethyl acetamide / 24 h / 25 °C / Inert atmosphere
3.1: triethylamine / 4-(N,N-dimethlyamino)pyridine / 3 h / Inert atmosphere
4.1: trifluoroacetic acid / 1 h / 20 °C / Inert atmosphere
5.1: triethylamine; hydrogen / [Rh(S)-phanephos(cod)]BF4 / ethanol / 6 h / 60 °C / 22502.3 Torr / Autoclave
6.1: triethylamine; diphenyl phosphoryl azide / toluene / 1 h / 80 °C / Inert atmosphere
6.2: 8 h / 50 °C / Reflux
7.1: hydrogenchloride; water / ethanol / 48 h / 70 °C
8.1: hydrogen / palladium 10 on activated carbon / methanol / 12 h / 760.05 Torr
8.2: Inert atmosphere
View Scheme
参考文献
CHEMO IBERICA, S.A.; TADDEI, Maurizio; RUSSO, Adele; CINI, Elena; RIVA, Renata; RASPARINI, Marcello; CARCONE, Luca; BANFI, Luca; VITALE, Romina; ROSEBLADE, Stephen; ZANOTTI-GEROSA, Antonio Carlo
Patent: WO2011/151442 A2, 2011 ;
反应条件
1.1: N,N-dimethyl acetamide / 24 h / 25 °C / Inert atmosphere
2.1: triethylamine / 4-(N,N-dimethlyamino)pyridine / 3 h / Inert atmosphere
3.1: trifluoroacetic acid / 1 h / 20 °C / Inert atmosphere
4.1: triethylamine; hydrogen / [Rh(S)-phanephos(cod)]BF4 / ethanol / 6 h / 60 °C / 22502.3 Torr / Autoclave
5.1: triethylamine; diphenyl phosphoryl azide / toluene / 1 h / 80 °C / Inert atmosphere
5.2: 8 h / 50 °C / Reflux
6.1: hydrogenchloride; water / ethanol / 48 h / 70 °C
7.1: hydrogen / palladium 10 on activated carbon / methanol / 12 h / 760.05 Torr
7.2: Inert atmosphere
View Scheme
参考文献
CHEMO IBERICA, S.A.; TADDEI, Maurizio; RUSSO, Adele; CINI, Elena; RIVA, Renata; RASPARINI, Marcello; CARCONE, Luca; BANFI, Luca; VITALE, Romina; ROSEBLADE, Stephen; ZANOTTI-GEROSA, Antonio Carlo
Patent: WO2011/151442 A2, 2011 ;
反应条件
1.1: triethylamine / 4-(N,N-dimethlyamino)pyridine / 3 h / Inert atmosphere
2.1: trifluoroacetic acid / 1 h / 20 °C / Inert atmosphere
3.1: triethylamine; hydrogen / [Rh(S)-phanephos(cod)]BF4 / ethanol / 6 h / 60 °C / 22502.3 Torr / Autoclave
4.1: triethylamine; diphenyl phosphoryl azide / toluene / 1 h / 80 °C / Inert atmosphere
4.2: 8 h / 50 °C / Reflux
5.1: hydrogenchloride; water / ethanol / 48 h / 70 °C
6.1: hydrogen / palladium 10 on activated carbon / methanol / 12 h / 760.05 Torr
6.2: Inert atmosphere
View Scheme
参考文献
CHEMO IBERICA, S.A.; TADDEI, Maurizio; RUSSO, Adele; CINI, Elena; RIVA, Renata; RASPARINI, Marcello; CARCONE, Luca; BANFI, Luca; VITALE, Romina; ROSEBLADE, Stephen; ZANOTTI-GEROSA, Antonio Carlo
Patent: WO2011/151442 A2, 2011 ;
反应条件
1.1: trifluoroacetic acid / 1 h / 20 °C / Inert atmosphere
2.1: triethylamine; hydrogen / [Rh(S)-phanephos(cod)]BF4 / ethanol / 6 h / 60 °C / 22502.3 Torr / Autoclave
3.1: triethylamine; diphenyl phosphoryl azide / toluene / 1 h / 80 °C / Inert atmosphere
3.2: 8 h / 50 °C / Reflux
4.1: hydrogenchloride; water / ethanol / 48 h / 70 °C
5.1: hydrogen / palladium 10 on activated carbon / methanol / 12 h / 760.05 Torr
5.2: Inert atmosphere
View Scheme
参考文献
CHEMO IBERICA, S.A.; TADDEI, Maurizio; RUSSO, Adele; CINI, Elena; RIVA, Renata; RASPARINI, Marcello; CARCONE, Luca; BANFI, Luca; VITALE, Romina; ROSEBLADE, Stephen; ZANOTTI-GEROSA, Antonio Carlo
Patent: WO2011/151442 A2, 2011 ;
反应条件
1.1: hydrogenchloride; tri-(hydroxymethyl)-methylamine; water; HLAP / 48 h / 40 °C / Enzymatic reaction
1.2: 20 °C / pH 3.5
2.1: lithium aluminium tetrahydride / tetrahydrofuran / 2 h / 40 °C / Inert atmosphere
2.2: 20 °C
3.1: triethylamine / toluene / 1.5 h / 0 - 20 °C / Inert atmosphere
4.1: sodium iodide / acetonitrile / Inert atmosphere; Reflux
5.1: N,N-dimethyl acetamide / 24 h / 25 °C / Inert atmosphere
6.1: triethylamine / 4-(N,N-dimethlyamino)pyridine / 3 h / Inert atmosphere
7.1: trifluoroacetic acid / 1 h / 20 °C / Inert atmosphere
8.1: triethylamine; hydrogen / [Rh(S)-phanephos(cod)]BF4 / ethanol / 6 h / 60 °C / 22502.3 Torr / Autoclave
9.1: triethylamine; diphenyl phosphoryl azide / toluene / 1 h / 80 °C / Inert atmosphere
9.2: 8 h / 50 °C / Reflux
10.1: hydrogenchloride; water / ethanol / 48 h / 70 °C
11.1: hydrogen / palladium 10 on activated carbon / methanol / 12 h / 760.05 Torr
11.2: Inert atmosphere
View Scheme
参考文献
CHEMO IBERICA, S.A.; TADDEI, Maurizio; RUSSO, Adele; CINI, Elena; RIVA, Renata; RASPARINI, Marcello; CARCONE, Luca; BANFI, Luca; VITALE, Romina; ROSEBLADE, Stephen; ZANOTTI-GEROSA, Antonio Carlo
Patent: WO2011/151442 A2, 2011 ;
反应条件
1.1: triethylamine / N,N-dimethyl aminopyride / methanol
2.1: sodium methylate / methanol / 0.5 h / 20 °C
2.2: 4 h / 80 °C
2.3: 1 h / 50 °C
View Scheme
参考文献
CARBODESIGN LLC
Patent: US2012/296100 A1, 2012 ;
反应条件
1.1: triethylamine / N,N-dimethyl aminopyride / methanol / 24 h
2.1: sodium methylate / methanol / 0.5 h / 20 °C
2.2: 4 h / 80 °C
2.3: 1 h / 50 °C
View Scheme
参考文献
CARBODESIGN LLC
Patent: US2012/296100 A1, 2012 ;
反应条件
1.1: oxalyl dichloride / N,N-dimethyl-formamide / acetonitrile / 4.5 h / 0 - 40 °C / Inert atmosphere
2.1: titanium tetrachloride / dichloromethane / 4 h / 0 - 40 °C / Inert atmosphere
3.1: triethylsilane; titanium tetrachloride / dichloromethane / 0 - 20 °C / Inert atmosphere
3.2: N,N-dimethylaminopyride / 24 h / 20 °C
4.1: sodium methylate / methanol / 0.5 h / 20 °C
4.2: 4 h / 80 °C
4.3: 1 h / 50 °C
View Scheme
参考文献
CARBODESIGN LLC
Patent: US2012/296100 A1, 2012 ;
反应条件
1: 3-methoxypropan-1-ol With sodium hydride
Inert atmosphere;
2: C26H40BrNO5 T=110 - 115°C; 3 h; Autoclave; Product distribution / selectivity;
参考文献
CARBODESIGN LLC
Patent: US2012/296100 A1, 2012 ;
Location in patent: Page/Page column 10 ;
反应条件
1: Mg
2: 23 percent / H2 / Pd(OH)2/C
3: 38 percent / TPAP; NMMO
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