p-Toluenesulfonic acid monohydrate → Bimatoprost

HRID 517405Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 517405
O.C1(C)C=CC(S(O)(=O)=O)=CC=1.[CH2:13]([NH:15][C:16](=[O:54])[CH2:17][CH2:18][CH2:19]/[CH:20]=[CH:21]\[CH2:22][C@H:23]1[C@@H:27]([OH:28])[CH2:26][C@@H:25]([O:29]C2CCCCO2)[C@@H:24]1/[CH:36]=[CH:37]/[C@@H:38]([O:47]C1CCCCO1)[CH2:39][CH2:40][C:41]1[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=1)[CH3:14]>CO>[CH3:14][CH2:13][NH:15][C:16]([CH2:17][CH2:18][CH2:19]/[CH:20]=[CH:21]\[CH2:22][C@@H:23]1[C@@H:24](/[CH:36]=[CH:37]/[C@@H:38]([OH:47])[CH2:39][CH2:40][C:41]2[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=2)[C@H:25]([OH:29])[CH2:26][C@@H:27]1[OH:28])=[O:54]

Komponenten

4

Edukt 2

HCID 521998p-Toluenesulfonic acid monohydrateHCID 58700551HCID 58700551, Verbindung

Produkt 1

HCID 5311027BimatoprostAusbeute 77,5 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Versuchsvorschrift

p-Toluenesulfonic acid monohydrate (0.03 g, 0.17 mmol) was added to a stirred solution of (5Z)-N-ethyl-7-((1R,2R,3R,5S)-5-hydroxy-2-((S,E)-5-phenyl-3-(tetrahydro-2H-pyran-2-yloxy)pent-1-enyl)-3-(tetrahydro-2H-pyran-2-yloxy)cyclopentyl)hept-5-enamide (2.0 g, 3.4 mmol) in methanol (20 mL). The mixture was stirred for 2 hours at room temperature. Then, the reaction mixture was washed with saturated aqueous solution of sodium bicarbonate (50 mL). The layers were separated and the aqueous layer was extracted with ethyl acetate (20 mL). The organic layers were dried over magnesium sulfate, filtered and concentrated under reduced pressure. The residue was crystallized from hexane and ethyl acetate to give Bimatoprost in a white crystalline form (77.5% yield). UPLC (ACQUITY UPLC BEH C18) analysis of the crude product showed that no 5,6-trans isomer, 15β-isomer or any other isomers were found.

Aufarbeitung

  1. washThen, the reaction mixture was washed with saturated aqueous solution of sodium bicarbonate (50 mL)
  2. customThe layers were separated
  3. extractionthe aqueous layer was extracted with ethyl acetate (20 mL)
  4. dry with materialThe organic layers were dried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was crystallized from hexane and ethyl acetate

Quellen und Nachweise

ORD-Eintrag
ord-d56a6dd0b1bd40d48809db71c1fba8f8
Quelldatensatz
uspto-grants-2015_08
Patentnummer
US09115109B2

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