[(1S,2R)-3-[[(4-硝基苯基)磺酰基](2-甲基丙基)氨基]-2-羟基-1-苯基甲基)丙基]氨基甲酸,(3S)-四氢-3-呋喃基酯合成路线 （共 36 条）
反应条件
triethylamine in dichloromethane
T=20°C; 4 h;
参考文献
LUPIN LIMITED; ARORA, Surinder, Kumar; SHABADE, Samir, Shanteshwar; KUMAR, Gaurav; RAY, Purna, Chandra; SINGH, Girij, Pal
Patent: WO2012/32389 A2, 2012 ;
Location in patent: Page/Page column 14 ;
反应条件
1: [(1S,2R)-3-[[(4-nitrophenyl)sulfonyl](2-methylpropyl)amino]-2-hydroxy-1-(phenylmethyl)propyl]carbamic acid tert-butyl ester With hydrogenchloride in dichloromethane
1.5 h;
2: (S)-3-tetrahydrofuranyl-N-oxysuccinimidyl carbonate With triethylamine in dichloromethane
T=20°C; 4 h; Further stages.;
参考文献
Kim; Bae; So; Yoo; Chang; Lee; Kang
Organic letters, 2001 , vol. 3, # 15 p. 2349 - 2351
反应条件
1.1: LDA / tetrahydrofuran; heptane; ethylbenzene / 1 h / -45 °C
1.2: tetrahydrofuran; heptane; ethylbenzene / 1 h / -45 °C
2.1: SO2Cl2 / CH2Cl2 / 0.5 h / 20 °C
3.1: 20.1 g / aq. HCOOH / 0.33 h / 80 °C
4.1: 77.2 percent / NaBH4 / CH2Cl2; methanol / 0.5 h / 0 °C
5.1: H2 / Pd/C / methanol / 4.5 h / 5 °C
6.1: aq. Na2CO3 / CH2Cl2 / 1 h / 20 °C
7.1: K2CO3 / methanol / 6 h / 20 °C
8.1: 7.55 g / ethanol / 3 h / Heating
9.1: aq. K2CO3 / CH2Cl2 / 8 h / 20 °C
View Scheme
参考文献
Honda, Yutaka; Katayama, Satoshi; Kojima, Mitsuhiko; Suzuki, Takayuki; Kishibata, Naomi; Izawa, Kunisuke
Organic and Biomolecular Chemistry, 2004 , vol. 2, # 14 p. 2061 - 2070
反应条件
1.1: 91 percent / aq. Na2CO3 / toluene / 1 h / 5 - 10 °C
2.1: LDA / tetrahydrofuran; heptane; ethylbenzene / 1 h / -45 °C
2.2: tetrahydrofuran; heptane; ethylbenzene / 1 h / -45 °C
3.1: SO2Cl2 / CH2Cl2 / 0.5 h / 20 °C
4.1: 20.1 g / aq. HCOOH / 0.33 h / 80 °C
5.1: 77.2 percent / NaBH4 / CH2Cl2; methanol / 0.5 h / 0 °C
6.1: H2 / Pd/C / methanol / 4.5 h / 5 °C
7.1: aq. Na2CO3 / CH2Cl2 / 1 h / 20 °C
8.1: K2CO3 / methanol / 6 h / 20 °C
9.1: 7.55 g / ethanol / 3 h / Heating
10.1: aq. K2CO3 / CH2Cl2 / 8 h / 20 °C
View Scheme
参考文献
Honda, Yutaka; Katayama, Satoshi; Kojima, Mitsuhiko; Suzuki, Takayuki; Kishibata, Naomi; Izawa, Kunisuke
Organic and Biomolecular Chemistry, 2004 , vol. 2, # 14 p. 2061 - 2070
反应条件
1: 77.2 percent / NaBH4 / CH2Cl2; methanol / 0.5 h / 0 °C
2: H2 / Pd/C / methanol / 4.5 h / 5 °C
3: aq. Na2CO3 / CH2Cl2 / 1 h / 20 °C
4: K2CO3 / methanol / 6 h / 20 °C
5: 7.55 g / ethanol / 3 h / Heating
6: aq. K2CO3 / CH2Cl2 / 8 h / 20 °C
View Scheme
参考文献
Honda, Yutaka; Katayama, Satoshi; Kojima, Mitsuhiko; Suzuki, Takayuki; Kishibata, Naomi; Izawa, Kunisuke
Organic and Biomolecular Chemistry, 2004 , vol. 2, # 14 p. 2061 - 2070
反应条件
1: H2 / Pd/C / methanol / 4.5 h / 5 °C
2: aq. Na2CO3 / CH2Cl2 / 1 h / 20 °C
3: K2CO3 / methanol / 6 h / 20 °C
4: 7.55 g / ethanol / 3 h / Heating
5: aq. K2CO3 / CH2Cl2 / 8 h / 20 °C
View Scheme
参考文献
Honda, Yutaka; Katayama, Satoshi; Kojima, Mitsuhiko; Suzuki, Takayuki; Kishibata, Naomi; Izawa, Kunisuke
Organic and Biomolecular Chemistry, 2004 , vol. 2, # 14 p. 2061 - 2070
反应条件
1: SO2Cl2 / CH2Cl2 / 0.5 h / 20 °C
2: 20.1 g / aq. HCOOH / 0.33 h / 80 °C
3: 77.2 percent / NaBH4 / CH2Cl2; methanol / 0.5 h / 0 °C
4: H2 / Pd/C / methanol / 4.5 h / 5 °C
5: aq. Na2CO3 / CH2Cl2 / 1 h / 20 °C
6: K2CO3 / methanol / 6 h / 20 °C
7: 7.55 g / ethanol / 3 h / Heating
8: aq. K2CO3 / CH2Cl2 / 8 h / 20 °C
View Scheme
参考文献
Honda, Yutaka; Katayama, Satoshi; Kojima, Mitsuhiko; Suzuki, Takayuki; Kishibata, Naomi; Izawa, Kunisuke
Organic and Biomolecular Chemistry, 2004 , vol. 2, # 14 p. 2061 - 2070
反应条件
1: 20.1 g / aq. HCOOH / 0.33 h / 80 °C
2: 77.2 percent / NaBH4 / CH2Cl2; methanol / 0.5 h / 0 °C
3: H2 / Pd/C / methanol / 4.5 h / 5 °C
4: aq. Na2CO3 / CH2Cl2 / 1 h / 20 °C
5: K2CO3 / methanol / 6 h / 20 °C
6: 7.55 g / ethanol / 3 h / Heating
7: aq. K2CO3 / CH2Cl2 / 8 h / 20 °C
View Scheme
参考文献
Honda, Yutaka; Katayama, Satoshi; Kojima, Mitsuhiko; Suzuki, Takayuki; Kishibata, Naomi; Izawa, Kunisuke
Organic and Biomolecular Chemistry, 2004 , vol. 2, # 14 p. 2061 - 2070
反应条件
1.1: toluene / 2.5 h / Heating
1.2: triethylamine / toluene / Heating
1.3: 70 percent / conc. HCl / toluene / 1.5 h / Heating
2.1: 80 percent / ethyl acetate; ethanol / 17 h / Heating
View Scheme
参考文献
Furfine, Eric S.; Baker, Christopher T.; Hale, Michael R.; Reynolds, David J.; Salisbury, Jo A.; Searle, Andy D.; Studenberg, Scott D.; Todd, Dan; Tung, Roger D.; Spaltenstein, Andrew
Antimicrobial Agents and Chemotherapy, 2004 , vol. 48, # 3 p. 791 - 798
反应条件
potassium carbonate in dichloromethane
T=20°C; 8 h;
参考文献
Honda, Yutaka; Katayama, Satoshi; Kojima, Mitsuhiko; Suzuki, Takayuki; Kishibata, Naomi; Izawa, Kunisuke
Organic and Biomolecular Chemistry, 2004 , vol. 2, # 14 p. 2061 - 2070
