顺式-4-羟基-D-脯氨酸合成路线 （共 35 条）
反应条件
1.1: TMSCl; diisopropylethylamine / CH2Cl2 / 1.5 h / Heating 1.2: CH2Cl2 / 0 - 20 °C 2.1: Jones reagent / acetone / 3 h / 20 °C View Scheme
参考文献
Patchett; Witkop
Journal of the American Chemical Society, 1957 , vol. 79, p. 185,190
反应条件
1: HCl 2: Et3N; 4-(dimethylamino)pyridine / acetone; H2O / 18 h / 20 °C 3: 68 percent / Jones reagent / acetone / 14 h / 20 °C View Scheme
参考文献
Journal of Medicinal Chemistry, , vol. 42, # 26 p. 5426 - 5436
反应条件
1: H2SO4 / 240 h / Heating 2: i-Pr2NEt / CH2Cl2 / Ambient temperature 3: 98 percent / oxalyl chloride, DMSO / CH2Cl2 / 2 h / -78 °C 4: ethanol; H2O / 48 h / 55 °C 5: 1.) aq. NaOH, 2.) SOCl2 / 1.) reflux, overnight, 2.) reflux, 3 d 6: 100 percent / CH2Cl2 / Ambient temperature 7: 85 percent / H2 / 5percent Pd/C / ethanol / 4 h / 3102.9 Torr / Ambient temperature 8: 1.) HCl (gas), 2.) 1 N aq. NaOH / 1.) Et2O, RT, 1 h, 2.) THF, RT, overnight View Scheme
参考文献
Monn, James A.; Valli, Matthew J.; Johnson, Bryan G.; Salhoff, Craig R.; Wright, Rebecca A.; Howe, Trevor; Bond, Ann; Lodge, David; Spangle, Larry A.; Paschal, Jonathan W.; Campbell, Jack B.; Griffey, Kelly; Tizzano, Joseph P.; Schoepp, Darryle D.
Journal of Medicinal Chemistry, 1996 , vol. 39, # 15 p. 2990 - 3000
反应条件
1: 82.5 percent / aq. NaOH / tetrahydrofuran / Ambient temperature
2: 92.4 percent / dioxane; diethyl ether / 0.25 h / 5 °C
3: 93.9 percent / Ph3P, DEAD / tetrahydrofuran / 42 h / Ambient temperature
4: 97.4 percent / LiBH4 / tetrahydrofuran / Ambient temperature
View Scheme
参考文献
Peterson, Mark L.; Vince, Robert
Journal of Medicinal Chemistry, 1991 , vol. 34, # 9 p. 2787 - 2797
反应条件
1.1: acetyl chloride / 8 h / Inert atmosphere; Reflux
2.1: 4-(N,N-dimethlyamino)pyridine; triethylamine / water; acetone
3.1: [bis(2-methoxyethyl)amino]-sulfur trifluoride / dichloromethane / 12 h / -78 - 20 °C
4.1: sodium hydroxide; water / tetrahydrofuran; methanol / 2 h
4.2: pH 3
View Scheme
参考文献
COMENTIS, INC.; BILCER, Geoffrey, M.; LILLY, John, C.; SWANSON, Lisa, M.
Patent: WO2011/130383 A1, 2011 ;
WO 2011/130383 A1
