Sodium Carbonate → Methyl 7-[5-((1E)(3S)-3-hydroxyoct-1-enyl)(1R,4R,5R)-4-hydroxy-2-oxocyclopentyl]heptanoate

HRID 428822

Reaktionsgleichung

Reaktionsgleichung von HRID 428822
[Si]([O:8][C@H:9]1[C@H:23](/[CH:24]=[CH:25]/[C@@H:26]([OH:32])[CH2:27][CH2:28][CH2:29][CH2:30][CH3:31])[C@@H:12]([CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][C:19]([O:21][CH3:22])=[O:20])[C:11](=[O:33])[CH2:10]1)(C(C)(C)C)(C)C.C(=O)([O-])[O-].[Na+].[Na+]>>[OH:8][C@H:9]1[C@H:23](/[CH:24]=[CH:25]/[C@@H:26]([OH:32])[CH2:27][CH2:28][CH2:29][CH2:30][CH3:31])[C@@H:12]([CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][C:19]([O:21][CH3:22])=[O:20])[C:11](=[O:33])[CH2:10]1

Komponenten

3

Edukt 2

HCID 10340Sodium CarbonateHCID 131722978HCID 131722978, Verbindung

Produkt 1

HCID 9864090Methyl 7-[5-((1E)(3S)-3-hydroxyoct-1-enyl)(1R,4R,5R)-4-hydroxy-2-oxocyclopentyl]heptanoateAusbeute 85 %

Reaktionsbedingungen

Temperatur
40 °C

Versuchsvorschrift

(−)-methyl(11R, 15S, 13E)-11-tert-butyldimethylsilyloxy-15-hydroxy-9-oxoprost-13-en-1-oate (481 mg, 1.0 mmol) was dissolved in 5 ml of a mixed solvent (ethyl acetate/water/tetrahydrofuran 6:3:1) and stirred at 40° C. for 2 h. The reaction mixture was poured into a saturated aqueous sodium carbonate cooled with ice and extracted with ethyl acetate (100 ml) two times. The combined organic layer was washed with a saturated aqueous sodium chloride, dried over anhydrous magnesium sulfate, and concentrated in vacuo to remove solvent. The residue was purified by silica gel column chromatography [ethyl acetate/hexane (2/1)] to give 312 mg (85% yield) of prostaglandin E1 methyl ester;

Aufarbeitung

  1. temperaturecooled with ice
  2. extractionextracted with ethyl acetate (100 ml) two times
  3. washThe combined organic layer was washed with a saturated aqueous sodium chloride
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationconcentrated in vacuo
  6. customto remove solvent
  7. customThe residue was purified by silica gel column chromatography [ethyl acetate/hexane (2/1)]

Quellen und Nachweise

ORD-Eintrag
ord-2b966432dd6d48f9b107f149ad16336b
Quelldatensatz
uspto-grants-2001_11
Patentnummer
US06313341B1

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