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 456801

Reaktionsgleichung

Reaktionsgleichung von HRID 456801
[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]

Komponenten

7

Edukt 4

HCID 8471TriethylamineHCID 10928Ethyl chloroformateHCID 160436Serotonin HydrochlorideHCID 5280363Dinoprost

Produkt 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]-amideAusbeute 68 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6344DichloromethaneLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

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 pyridiniump-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%).

Aufarbeitung

  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 pyridiniump-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

Quellen und Nachweise

ORD-Eintrag
ord-c63b984579e0416783772af0bfe371cd
Quelldatensatz
uspto-grants-2007_03
Patentnummer
US07186744B2

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