Alprostadil → Pga1

HRID 26304

Reaktionsgleichung

Reaktionsgleichung von HRID 26304
[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:14]([CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][C:21]([OH:23])=[O:22])[C:12](=[O:13])[CH2:11][C@H:10]1O>C(O)(=O)C.O>[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:14]([CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][C:21]([OH:23])=[O:22])[C:12](=[O:13])[CH:11]=[CH:10]1

Komponenten

3

Edukt 1

HCID 5280723Alprostadil

Produkt 1

HCID 5281912Pga1

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 21899381Acetic acid--water (1/1)Lösungsmittel

Versuchsvorschrift

A 125 mg (0.3 mmol) portion of the prostaglandin E1 analogue of Example 3 (14-Phenyl-11α,15R-dihydroxy-9-oxoprost-10,13E-dien-1-oic acid) was stirred into 10 ml of acetic acid-water (2:1) at 50° C. under an inert atmosphere. Progress of the reaction was followed by thin layer chromatography. After 48 hours, the reaction mixture was extracted with ether. Ether layers obtained were combined and washed to neutrality with brine. Removal of the solvent yielded a yellow oil. The oil was azeotroped with toluene and chromatographed on 70 g SG-60, and eluted with benzene-ethanol (19:1) to yield 102 mg of the PGA1 analogue.

Aufarbeitung

  1. extractionthe reaction mixture was extracted with ether
  2. customEther layers obtained
  3. washwashed
  4. customRemoval of the solvent
  5. customyielded a yellow oil
  6. customThe oil was azeotroped with toluene
  7. customchromatographed on 70 g SG-60
  8. washeluted with benzene-ethanol (19:1)

Quellen und Nachweise

ORD-Eintrag
ord-2c28d4190b6e46498a16bbc8b4c01369
Quelldatensatz
uspto-grants-1979_04
Patentnummer
US04149007

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