Misoprostol → HCID 53675869, Verbindung

HRID 1587530

Reaktionsgleichung

Reaktionsgleichung von HRID 1587530
[CH3:1][O:2][C:3](=[O:27])[CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][C@@H:10]1[C@@H:14](/[CH:15]=[CH:16]/[CH2:17][C:18]([OH:24])([CH3:23])[CH2:19][CH2:20][CH2:21][CH3:22])[C@H:13]([OH:25])[CH2:12][C:11]1=[O:26]>C(O)C.[Pd]>[CH3:1][O:2][C:3](=[O:27])[CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][C@@H:10]1[C@@H:14]([CH2:15][CH2:16][CH2:17][C:18]([OH:24])([CH3:23])[CH2:19][CH2:20][CH2:21][CH3:22])[C@H:13]([OH:25])[CH2:12][C:11]1=[O:26]

Komponenten

4

Edukt 1

HCID 5282381Misoprostol

Produkt 1

HCID 53675869HCID 53675869, VerbindungAusbeute 85,5 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23938PalladiumKatalysatorHCID 702EthanolLösungsmittel

Versuchsvorschrift

(±) methyl-11α,16-dihydroxy-16-methyl-9-oxoprost13E-en-1-oate (100mg) in 15 ml of ethanol containing 100 mg of 4% palladium on carbon is hydrogenated at room temperature and atmospheric pressure for 24 minutes. The solution is filtered and evaporated. The residue is chromatographed on silica gel (60% ethyl acetate/40% hexane as eluent) to give 86 mg of desired product as a viscous oil. 1H NMR (CDCl3): ∂0.93 (t, C.20CH3); 1.18 (d,C.16CH3 3.68 (s, OCH3); 4.17 (q C.11 H).

Aufarbeitung

  1. customis hydrogenated at room temperature
  2. filtrationThe solution is filtered
  3. customevaporated
  4. customThe residue is chromatographed on silica gel (60% ethyl acetate/40% hexane as eluent)

Quellen und Nachweise

ORD-Eintrag
ord-75469d0a776441b7b94fd3cb24712d28
Quelldatensatz
uspto-grants-1993_06
Patentnummer
US05218139

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