(1R,4S)-(+)-4-氨基环戊-2-烯甲酸合成路线 （共 9 条）
反应条件
cloned (+)-γ-lactamase T=25°C; Ring cleavage; pH=7.5; 1 h;
参考文献
Bioorganic and Medicinal Chemistry, , vol. 7, # 10 p. 2163 - 2168
反应条件
hydrogenchloride Hydrolysis; 12 h;
参考文献
Journal of Medicinal Chemistry, , vol. 42, # 22 p. 4725 - 4728
反应条件
1.1: 85 percent / SOCl2 / 2 h / 0 - 20 °C 2.1: 96 percent / NEt3 / CH2Cl2 / 2 h / 0 °C 3.1: NBS / tetrahydrofuran; H2O / 20 °C 4.1: KOH / methanol; H2O / 90 °C 4.2: H2O; tetrahydrofuran / 5 - 20 °C / pH 10.5 5.1: H2 / Pd/C / methanol / 20 °C / 1810.02 Torr 6.1: NEt3 / methanol / 5 - 20 °C View Scheme
参考文献
Smith, Mark E.B.; Lloyd, Michael C.; Derrien, Nadine; Lloyd, Richard C.; Taylor, Stephen J.C.; Chaplin, David A.; Casy, Guy; McCague, Raymond
Tetrahedron Asymmetry, 2001 , vol. 12, # 5 p. 703 - 705
反应条件
1.1: 85 percent / SOCl2 / 2 h / 0 - 20 °C 2.1: 96 percent / NEt3 / CH2Cl2 / 2 h / 0 °C 3.1: NBS / tetrahydrofuran; H2O / 20 °C 4.1: KOH / methanol; H2O / 90 °C 4.2: H2O; tetrahydrofuran / 5 - 20 °C / pH 10.5 5.1: H2 / Pd/C / methanol / 20 °C / 1810.02 Torr 6.1: NEt3 / methanol / 5 - 20 °C 7.1: TEA; DMAP / CH2Cl2 / 5 °C 8.1: dimethylformamide / 60 °C 9.1: NaOMe / methanol / 5 °C View Scheme
参考文献
Smith, Mark E.B.; Lloyd, Michael C.; Derrien, Nadine; Lloyd, Richard C.; Taylor, Stephen J.C.; Chaplin, David A.; Casy, Guy; McCague, Raymond
Tetrahedron Asymmetry, 2001 , vol. 12, # 5 p. 703 - 705
反应条件
hydrogen; palladium on activated charcoal in acetic acid
参考文献
Evans, Chris; McCague, Ray; Roberts, Stanley M.; Sutherland, Alan G.
Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999), 1991 , # 3 p. 656 - 657
反应条件
1.1: 85 percent / SOCl2 / 2 h / 0 - 20 °C 2.1: 96 percent / NEt3 / CH2Cl2 / 2 h / 0 °C 3.1: NBS / tetrahydrofuran; H2O / 20 °C 4.1: KOH / methanol; H2O / 90 °C 4.2: H2O; tetrahydrofuran / 5 - 20 °C / pH 10.5 5.1: NEt3 / methanol / 5 - 20 °C 6.1: H2; {(S,S)-[MeDuPHOS]-Rh(COD)}BF4 / methanol / 20 °C / 3878.61 Torr View Scheme
参考文献
Smith, Mark E.B.; Lloyd, Michael C.; Derrien, Nadine; Lloyd, Richard C.; Taylor, Stephen J.C.; Chaplin, David A.; Casy, Guy; McCague, Raymond
Tetrahedron Asymmetry, 2001 , vol. 12, # 5 p. 703 - 705
反应条件
1.1: 85 percent / SOCl2 / 2 h / 0 - 20 °C 2.1: 96 percent / NEt3 / CH2Cl2 / 2 h / 0 °C 3.1: NBS / tetrahydrofuran; H2O / 20 °C 4.1: KOH / methanol; H2O / 90 °C 4.2: H2O; tetrahydrofuran / 5 - 20 °C / pH 10.5 5.1: NEt3 / methanol / 5 - 20 °C 6.1: H2; {(S,S)-[MeDuPHOS]-Rh(COD)}BF4 / methanol / 20 °C / 3878.61 Torr 7.1: TEA; DMAP / CH2Cl2 / 5 °C 8.1: dimethylformamide / 60 °C 9.1: NaOMe / methanol / 5 °C View Scheme
参考文献
Smith, Mark E.B.; Lloyd, Michael C.; Derrien, Nadine; Lloyd, Richard C.; Taylor, Stephen J.C.; Chaplin, David A.; Casy, Guy; McCague, Raymond
Tetrahedron Asymmetry, 2001 , vol. 12, # 5 p. 703 - 705
反应条件
1: With sodium hydrogencarbonate in tetrahydrofuran; water 2: With hydrogenchloride in water T=0°C; pH=3; Acidic conditions;
参考文献
MERCK and CO., INC.
Patent: WO2005/110409 A2, 2005 ;
Location in patent: Page/Page column 30 ;
WO 2005/110409 A2
反应条件
1: 85 percent / SOCl2 / 2 h / 0 - 20 °C
2: 96 percent / NEt3 / CH2Cl2 / 2 h / 0 °C
View Scheme
参考文献
Qiu, Jian; Pingsterhaus, Joyce M.; Silverman, Richard B.
Journal of Medicinal Chemistry, 1999 , vol. 42, # 22 p. 4725 - 4728
