m-Chloroperbenzoic acid → HCID 14823693, Verbindung

HRID 372411Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 372411
[F:1][C@:2]12[C@@H:19]([OH:20])[CH2:18][C@@:16]3([CH3:17])[C@@H:12]([CH2:13][CH:14]=[C:15]3[S:21][CH3:22])[C@@H:11]1[CH2:10][CH2:9][C:8]1[C@:3]2([CH3:24])[CH:4]=[CH:5][C:6](=[O:23])[CH:7]=1.ClC1C=CC=C(C(OO)=[O:33])C=1>C(Cl)(Cl)Cl>[F:1][C@:2]12[C@@H:19]([OH:20])[CH2:18][C@@:16]3([CH3:17])[C@@H:12]([CH2:13][CH:14]=[C:15]3[S:21]([CH3:22])=[O:33])[C@@H:11]1[CH2:10][CH2:9][C:8]1[C@:3]2([CH3:24])[CH:4]=[CH:5][C:6](=[O:23])[CH:7]=1

Komponenten

4

Edukt 2

HCID 70297m-Chloroperbenzoic acidHCID 14823699HCID 14823699, Verbindung

Produkt 1

HCID 14823693HCID 14823693, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6212ChloroformLösungsmittel2×

Versuchsvorschrift

To a stirred solution of 1.0 g of 9-fluoro-11β-hydroxy-17-(methylthio)androsta-1,4,16-trien-3-one (see Example 1B) in chloroform (500 ml) is added a solution of 85% m-chloroperbenzoic acid (552 mg) in chloroform (10 ml) in the course of 3.0 minutes. In less than 10 minutes, the peracid and the starting steroid disappear. The solution is then washed with a dilute potassium carbonate solution and water, dried, concentrated (to about 10 ml) and diluted with ethyl acetate resulting in the precipitation of small, light needles of the analytical specimen of the title compound, (1.0 g), melting point 268°-269° C (dec.). This is a mixture of the two sulfinyl isomers.

Aufarbeitung

  1. waitIn less than 10 minutes
  2. washThe solution is then washed with a dilute potassium carbonate solution and water
  3. customdried
  4. concentrationconcentrated (to about 10 ml)
  5. additiondiluted with ethyl acetate resulting in the precipitation of small, light needles of the analytical specimen of the title compound, (1.0 g), melting point 268°-269° C (dec.)
  6. additiona mixture of the two sulfinyl isomers

Quellen und Nachweise

ORD-Eintrag
ord-a9c08ff645414180ad6d20aea18cc714
Quelldatensatz
uspto-grants-1978_05
Patentnummer
US04091036

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