吡啶 → 2-[2-(4-Fluorophenyl)acetyl]-4-(4-nitro-phenoxycarbonyloxy)-pyrazolidine-1-carboxylic acid benzyl ester

HRID 7662

反应方程式

HRID 7662 反应方程式
[CH2:1]([O:8][C:9]([N:11]1[CH2:15][CH:14]([OH:16])[CH2:13][N:12]1[C:17](=[O:26])[CH2:18][C:19]1[CH:24]=[CH:23][C:22]([F:25])=[CH:21][CH:20]=1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl[C:28]([O:30][C:31]1[CH:36]=[CH:35][C:34]([N+:37]([O-:39])=[O:38])=[CH:33][CH:32]=1)=[O:29].N1C=CC=CC=1>ClCCl.O>[CH2:1]([O:8][C:9]([N:11]1[CH2:15][CH:14]([O:16][C:28]([O:30][C:31]2[CH:32]=[CH:33][C:34]([N+:37]([O-:39])=[O:38])=[CH:35][CH:36]=2)=[O:29])[CH2:13][N:12]1[C:17](=[O:26])[CH2:18][C:19]1[CH:24]=[CH:23][C:22]([F:25])=[CH:21][CH:20]=1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

参与物

6

反应物 3

HCID 1049吡啶HCID 82129对硝基苯基氯甲酸酯HCID 207247442-[2-(4-Fluorophenyl)acetyl]-4-hydroxypyrazolidine-1-carboxylic acid benzyl ester

产物 1

HCID 207247432-[2-(4-Fluorophenyl)acetyl]-4-(4-nitro-phenoxycarbonyloxy)-pyrazolidine-1-carboxylic acid benzyl ester收率 86%

试剂、催化剂与溶剂 2

HCID 962聚[6-[4-(4-氰基苯基)苯氧基]己基甲基丙烯酸酯]溶剂HCID 6344二氯甲烷溶剂

反应条件

温度
0 °C

实验过程

2-[2-(4-Fluorophenyl)acetyl]-4-hydroxy-pyrazolidine-1-carboxylic acid benzyl ester, 38, (366 mg, 1.02 mmol) is dissolved in dichloromethane (10 mL). The solution is cooled to 0° C. and p-nitrophenyl chloroformate (411 mg, 2.04 mmol) is added in one portion. The solution is stirred at 0° C., and pyridine (198 μL, 2.45 mmol) added. Stirring is continued at 0° C. for 1 hour followed by stirring at room temperature for 12 hours. The reaction is diluted with water (40 mL) and extracted with dichloromethane (40 mL). The organic layer is washed with 0.5 N NaOH (2×40 mL). The combined aqueous layers are back-extracted extracted with dichloromethane (30 mL). The combined organic layers are washed with brine (30 mL), dried, filtered, and concentrated in vacuo. The crude material is purified over silica (3:1 to 2:1 to 1:1 hexane/ethyl acetate) to afford 462 mg (86% yield) of the desired product as a white foam.

后处理

  1. stirringStirring
  2. stirringby stirring at room temperature for 12 hours
  3. extractionextracted with dichloromethane (40 mL)
  4. washThe organic layer is washed with 0.5 N NaOH (2×40 mL)
  5. extractionThe combined aqueous layers are back-extracted
  6. extractionextracted with dichloromethane (30 mL)
  7. washThe combined organic layers are washed with brine (30 mL)
  8. customdried
  9. filtrationfiltered
  10. concentrationconcentrated in vacuo
  11. customThe crude material is purified over silica (3:1 to 2:1 to 1:1 hexane/ethyl acetate)

来源与证据

ORD记录
ord-07899571ac004176a04f3732b5db25f0
来源数据集
uspto-grants-2006_08
专利号
US07087615B2

关联笔记

加载中…