Hydrochloric Acid → 9-Oxo-15S-hydroxy-5Z,8(12),13E,17Z-prostatetraenoic acid

HRID 1076079Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1076079
[CH3:1][CH2:2]/[CH:3]=[CH:4]\[CH2:5][C@H:6]([OH:25])/[CH:7]=[CH:8]/[C@@H:9]1[C@@H:14]([CH2:15]/[CH:16]=[CH:17]\[CH2:18][CH2:19][CH2:20][C:21]([OH:23])=[O:22])[C:12](=[O:13])[CH2:11][C@H:10]1O.[OH-].[K+].Cl>C(O)C>[CH3:1][CH2:2]/[CH:3]=[CH:4]\[CH2:5][C@H:6]([OH:25])/[CH:7]=[CH:8]/[C:9]1[CH2:10][CH2:11][C:12](=[O:13])[C:14]=1[CH2:15]/[CH:16]=[CH:17]\[CH2:18][CH2:19][CH2:20][C:21]([OH:23])=[O:22]

Komponenten

5

Edukt 3

HCID 313Hydrochloric AcidHCID 14797Potassium HydroxideHCID 5280937Prostaglandin E3

Produkt 1

HCID 52831139-Oxo-15S-hydroxy-5Z,8(12),13E,17Z-prostatetraenoic acid

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Reaktionsbedingungen

Temperatur
10 °C

Versuchsvorschrift

A solution of racemic PGE3 (200 mg.) in 100 ml. of 50% aqueous ethanol containing 10 grams of potassium hydroxide is kept at 25° C. for 10 hours under notrogen. Then, the solution is cooled to 10° C. and neutralized by addition of 3 normal hydrochloric acid at 10° C. The resulting solution is extracted repeatedly with ethyl acetate, and the combined ethyl acetate extracts are washed with water and then with saturated aqueous sodium chloride solution, dried, and evaporated to give racemic PGB3.

Aufarbeitung

  1. extractionThe resulting solution is extracted repeatedly with ethyl acetate
  2. washthe combined ethyl acetate extracts are washed with water
  3. dry with materialwith saturated aqueous sodium chloride solution, dried
  4. customevaporated

Quellen und Nachweise

ORD-Eintrag
ord-03f36092e84743d7891e50c35a0a07d0
Quelldatensatz
uspto-grants-1976_05
Patentnummer
US03954851

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