2-Methyl-2-butene → Epristeride

HRID 1940425Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1940425
[OH2:1].O.P([O-])([O-])([O-])=O.[Na+].[Na+].[Na+].Cl([O-])=O.[Na+].CC(=CC)C.[C:20]([NH:24][C:25]([C@H:27]1[CH2:32][CH2:31][C@H:30]2[C@H:33]3[C@H:43]([CH2:44][CH2:45][C@:28]12[CH3:29])[C@:41]1([CH3:42])[C:36]([CH:37]=[C:38]([CH:46]=[O:47])[CH2:39][CH2:40]1)=[CH:35][CH2:34]3)=[O:26])([CH3:23])([CH3:22])[CH3:21]>O.C(O)(C)(C)C>[C:20]([NH:24][C:25]([C@H:27]1[CH2:32][CH2:31][C@H:30]2[C@H:33]3[C@H:43]([CH2:44][CH2:45][C@:28]12[CH3:29])[C@:41]1([CH3:42])[C:36]([CH:37]=[C:38]([C:46]([OH:1])=[O:47])[CH2:39][CH2:40]1)=[CH:35][CH2:34]3)=[O:26])([CH3:21])([CH3:22])[CH3:23]

Komponenten

7

Edukt 4

HCID 105532-Methyl-2-buteneHCID 18623014Trisodium;phosphate;dihydrateHCID 23668197Sodium ChloriteHCID 86749645N-t-Butyl-3-formylandrosta-3,5-diene-17beta-carboxamide

Produkt 1

HCID 68741Epristeride

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 6386tert-ButanolLösungsmittel

Versuchsvorschrift

600 mg of sodium phosphate dihydrate and 1.2 g of sodium chlorite were added, in that order, at room temperature to a mixture of 7.5 ml of t-butanol, 2.0 ml of water and 1 ml of 2-methyl-2-butene containing 400 mg of N-t-butyl-3-formylandrosta-3,5-diene-17β-carboxamide (prepared as described in Preparation 6). The reaction mixture was then stirred for 15 minutes. At the end of this time, the reaction mixture was quenched by pouring it into a ice-cooled aqueous solution of sodium thiosulfate; it was then made acidic by the addition of 1N aqueous hydrochloric acid, and extracted with ethyl acetate three times. The combined organic extracts were washed with water and with a saturated aqueous solution of sodium chloride, dried over anhydrous magnesium sulfate, and concentrated by evaporation under reduced pressure. The resulting residue was crystallized by the addition of diethyl ether, to give 225 mg of the title compound.

Aufarbeitung

  1. customAt the end of this time, the reaction mixture was quenched
  2. additionby pouring it into a ice-
  3. temperaturecooled aqueous solution of sodium thiosulfate
  4. additionmade acidic by the addition of 1N aqueous hydrochloric acid
  5. extractionextracted with ethyl acetate three times
  6. washThe combined organic extracts were washed with water and with a saturated aqueous solution of sodium chloride
  7. dry with materialdried over anhydrous magnesium sulfate
  8. concentrationconcentrated by evaporation under reduced pressure
  9. customThe resulting residue was crystallized by the addition of diethyl ether

Quellen und Nachweise

ORD-Eintrag
ord-fd338b862e354ea39c0b273a4c0384ef
Quelldatensatz
uspto-grants-1997_12
Patentnummer
US05698720

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