Cortisol → cortienic acid

HRID 1695541

Reaktionsgleichung

Reaktionsgleichung von HRID 1695541
I(O)(O)(O)(O)(O)=[O:2].[OH:8][C@@H:9]1[C@H:25]2[C@@H:16]([CH2:17][CH2:18][C:19]3[C@:24]2([CH3:26])[CH2:23][CH2:22][C:21](=[O:27])[CH:20]=3)[C@H:15]2[C@@:11]([CH3:33])([C@@:12]([OH:32])([C:28](=[O:31])CO)[CH2:13][CH2:14]2)[CH2:10]1>O.C1COCC1.[OH-].[Na+]>[OH:8][C@@H:9]1[C@H:25]2[C@@H:16]([CH2:17][CH2:18][C:19]3[C@:24]2([CH3:26])[CH2:23][CH2:22][C:21](=[O:27])[CH:20]=3)[C@H:15]2[C@@:11]([CH3:33])([C@@:12]([OH:32])([C:28]([OH:2])=[O:31])[CH2:13][CH2:14]2)[CH2:10]1

Komponenten

6

Edukt 2

HCID 5754CortisolHCID 25289Orthoperiodic acid

Produkt 1

HCID 11382469cortienic acidAusbeute 95 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 962WaterLösungsmittelHCID 8028TetrahydrofuranLösungsmittelHCID 14798Sodium HydroxideLösungsmittel

Versuchsvorschrift

A solution of orthoperiodic acid (21.4 g, 94 mmol) in water (80 ml) was added to a solution of (8S,9S,10R,11S,13S,14S,17R)-11,17-dihydroxy-17-(2-hydroxyacetyl)-10,13-dimethyl-6,7,8,9,10,11,12,13,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3(2H)-one (Hydrocortisone, 17.0 g, 46.9 mmol) in THF (350 ml), and the reaction mixture was stirred at room temperature in an open flask for 2 hours. Then the mixture was poured onto ice. After the ice had molten, the mixture was extracted with ethyl acetate (3 times 150 ml). Evaporation of the solvent gave a white solid, which was dissolved in aqueous NaOH (1 M, 150 ml). The solution was washed with ethyl acetate, and acidified with conc. aqueous HCl. The precipitate formed was collected by filtration, and dried on the sinter overnight to afford the target compound as an off-white powder (15.51 g, 95%).

Aufarbeitung

  1. additionThen the mixture was poured onto ice
  2. extractionthe mixture was extracted with ethyl acetate (3 times 150 ml)
  3. customEvaporation of the solvent
  4. customgave a white solid, which
  5. washThe solution was washed with ethyl acetate
  6. customThe precipitate formed
  7. filtrationwas collected by filtration
  8. customdried on the sinter overnight

Quellen und Nachweise

ORD-Eintrag
ord-bf9659f1d0df42fcb50558f13113df1e
Quelldatensatz
uspto-grants-2012_04
Patentnummer
US08163724B2

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