Morpholine → HCID 69659315, 화합물

HRID 1791000

반응식

HRID 1791000 반응식
[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]

참가 물질

6

반응물 4

HCID 8083MorpholineHCID 25517Ammonium ChlorideHCID 682631,1'-CarbonyldiimidazoleHCID 6917951Beraprost

생성물 1

HCID 69659315HCID 69659315, 화합물수율 48%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

반응 조건

온도
50 °C

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-a4f667ad199b4df4a69d9ad291606bb7
출처 데이터셋
uspto-grants-2006_07
특허 번호
US07071359B1

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