Triethylamine → (Z)-7-[(1R,2R,3R,5S)-3,5-Dihydroxy-2-((E)-(S)-3-hydroxy-oct-1-enyl)-cyclopentyl]-hept-5-enoic acid [2-(5-hydroxy-1H-indol-3-yl)-ethyl]-amide

HRID 55777

반응식

HRID 55777 반응식
[CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][C@H:6]([OH:25])/[CH:7]=[CH:8]/[C@@H:9]1[C@@H:13]([CH2:14]/[CH:15]=[CH:16]\[CH2:17][CH2:18][CH2:19][C:20]([OH:22])=O)[C@@H:12]([OH:23])[CH2:11][C@H:10]1[OH:24].C(N(CC)CC)C.C(OC(Cl)=O)C.[CH:39]1[C:44]([OH:45])=[CH:43][C:42]2[C:46]([CH2:49][CH2:50][NH2:51])=[CH:47][NH:48][C:41]=2[CH:40]=1.Cl>C(Cl)Cl.C(OCC)(=O)C>[OH:45][C:44]1[CH:43]=[C:42]2[C:41](=[CH:40][CH:39]=1)[NH:48][CH:47]=[C:46]2[CH2:49][CH2:50][NH:51][C:20](=[O:22])[CH2:19][CH2:18][CH2:17]/[CH:16]=[CH:15]\[CH2:14][C@H:13]1[C@@H:12]([OH:23])[CH2:11][C@@H:10]([OH:24])[C@@H:9]1/[CH:8]=[CH:7]/[C@@H:6]([OH:25])[CH2:5][CH2:4][CH2:3][CH2:2][CH3:1]

참가 물질

7

반응물 4

HCID 8471TriethylamineHCID 10928Ethyl chloroformateHCID 160436Serotonin HydrochlorideHCID 5280363Dinoprost

생성물 1

HCID 11411264(Z)-7-[(1R,2R,3R,5S)-3,5-Dihydroxy-2-((E)-(S)-3-hydroxy-oct-1-enyl)-cyclopentyl]-hept-5-enoic acid [2-(5-hydroxy-1H-indol-3-yl)-ethyl]-amide수율 68%

시약·촉매·용매 2

HCID 6344Dichloromethane용매HCID 8857Ethyl Acetate용매

반응 조건

온도
0 °C

실험 절차

A solution of the protected prostaglandin F2α (500 mg, 0.825 mmol) in CH2Cl2 (4.5 mL) was treated with triethylamine (290 μL, 2.06 mmol) with stirring and cooled to 0° C. Ethylchloroformate (87 μL, 0.907 mmol) was then added and after 15 minutes the reaction was warmed to room temperature. Serotonin hydrochloride (211 mg, 0.99 mmol) was added and stirred for 16 hours. The reaction was then diluted with ethyl acetate and washed with HCl (1 N), saturated sodium bicarbonate, and brine. The organic portion was dried (MgSO4), filtered and concentrated in vacuo. The residue was diluted with methanol and pyridinium p-toluenesulfonate (PPTs) (100 mg) was added and the solution was stirred for 24 hours. The solvent was then removed in vacuo, and the residue was diluted with ethyl acetate and washed with HCl (1 N), saturated sodium bicarbonate, and brine. The organic portion was dried (MgSO4), filtered and concentrated in vacuo. Flash column chromatography (silica gel, 19:1 ethyl acetate:methanol) gave (Z)-7-[(1R,2R,3R,5S)-3,5-Dihydroxy-2-((E)-(S)-3-hydroxy-oct-1-enyl)-cyclopentyl]-hept-5-enoic acid [2-(5-hydroxy-1H-indol-3-yl)-ethyl]-amide (Compound 3) (287 mg, 68%).

후처리

  1. temperaturewas warmed to room temperature
  2. stirringstirred for 16 hours
  3. washwashed with HCl (1 N), saturated sodium bicarbonate, and brine
  4. dry with materialThe organic portion was dried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. additionThe residue was diluted with methanol and pyridinium p-toluenesulfonate (PPTs) (100 mg)
  8. additionwas added
  9. stirringthe solution was stirred for 24 hours
  10. customThe solvent was then removed in vacuo
  11. additionthe residue was diluted with ethyl acetate
  12. washwashed with HCl (1 N), saturated sodium bicarbonate, and brine
  13. dry with materialThe organic portion was dried (MgSO4)
  14. filtrationfiltered
  15. concentrationconcentrated in vacuo

출처 및 근거

ORD 기록
ord-e0d892948c5a435b9b638f057f1499a2
출처 데이터셋
uspto-grants-2016_09
특허 번호
US09433627B2

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