1,4-氧氮六环 → HCID 69659315，化合物

HRID 1791000

反应方程式

HRID 1791000 反应方程式
[OH:1][C@@H:2]1[CH2:19][C@@H:5]2[O:6][C:7]3[C:12]([CH2:13][CH2:14][CH2:15][C:16](O)=O)=[CH:11][CH:10]=[CH:9][C:8]=3[C@@H:4]2[C@H:3]1/[CH:20]=[CH:21]/[C@@H:22]([OH:29])[CH:23]([CH3:28])[CH2:24][C:25]#[C:26][CH3:27].C(N1C=CN=C1)(N1C=CN=C1)=O.[NH:42]1[CH2:47][CH2:46][O:45][CH2:44][CH2:43]1.[Cl-].[NH4+]>CN(C)C=O>[OH:1][C@@H:2]1[CH2:19][C@@H:5]2[O:6][C:7]3[C:12]([CH2:13][CH2:14][CH2:15][CH2:16][N:42]4[CH2:47][CH2:46][O:45][CH2:44][CH2:43]4)=[CH:11][CH:10]=[CH:9][C:8]=3[C@@H:4]2[C@H:3]1/[CH:20]=[CH:21]/[C@@H:22]([OH:29])[CH:23]([CH3:28])[CH2:24][C:25]#[C:26][CH3:27]

参与物

6

反应物 4

HCID 80831,4-氧氮六环HCID 25517氯化铵HCID 68263N,N'-羰基二咪唑HCID 6917951Beraprost

产物 1

HCID 69659315HCID 69659315，化合物收率 48%

试剂、催化剂与溶剂 1

HCID 6228N,N-二甲基甲酰胺溶剂

反应条件

温度
50 °C

实验过程

10 mg of (1R,2R,3aS,8bS)-2,3,3a,8b-tetrahydro-2-hydroxy-1-[(3S,1E)-3-hydroxy-4-methyl-1-octene-6-ynyl]-5-(3-carboxypropyl)-1H-cyclopenta[b]benzofuran was taken and was dissolved in 2 mL of dimethylformamide. After addition of 8.1 mg of 1,1′-carbonyldiimidazole, it was stirred at 50° C. for 1 hour. It was cooled to ambient temperature, and 50 mg morpholine was added. After stirring at 50° C. for 1 hour, an aqueous solution saturated with ammonium chloride was added and extracted with ethyl acetate. The organic layer was washed with a saturated saline solution, and dried with anhydrous sodium sulfate. After filtration and concentration, 2 mL of tetrahydrofurane was added. While stirring on ice, 9.5 mg of lithium aluminium hydride was added and stirring continued at 0° C. for 15 minutes, then at 50° C. for 1 hour. While stirring at ambient temperature, 100 μL of an aqueous solution saturated with sodium sulfate was added, then 400 mg of anhydrous sodium sulfate was added, and stirred for 1 hour. A filtration was performed over celite, and after washing the residue with ethyl acetate, the filtrate was concentrated and subjected to a silicagel column chromatography, to obtain 5.3 mg of the compound presented in the title (48% yield).

后处理

  1. temperatureIt was cooled to ambient temperature
  2. stirringAfter stirring at 50° C. for 1 hour
  3. extractionextracted with ethyl acetate
  4. washThe organic layer was washed with a saturated saline solution
  5. dry with materialdried with anhydrous sodium sulfate
  6. filtrationAfter filtration and concentration, 2 mL of tetrahydrofurane
  7. additionwas added
  8. stirringWhile stirring on ice, 9.5 mg of lithium aluminium hydride
  9. additionwas added
  10. stirringstirring
  11. waitcontinued at 0° C. for 15 minutes
  12. waitat 50° C. for 1 hour
  13. stirringWhile stirring at ambient temperature
  14. addition100 μL of an aqueous solution saturated with sodium sulfate was added
  15. addition400 mg of anhydrous sodium sulfate was added
  16. stirringstirred for 1 hour
  17. filtrationA filtration
  18. washafter washing the residue with ethyl acetate
  19. concentrationthe filtrate was concentrated

来源与证据

ORD记录
ord-a4f667ad199b4df4a69d9ad291606bb7
来源数据集
uspto-grants-2006_07
专利号
US07071359B1

关联笔记

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