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Acetic Acid → 21-Acetoxy-9alpha-hydroxypregna-4,16-diene-3,20-dione

HRID 1613971
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1613971
[C:1]([O:4][CH2:5][C:6](=NO)[C:7]1[C@:24]2([CH3:25])[C@H:10]([C@H:11]3[C@:21]([OH:26])([CH2:22][CH2:23]2)[C@:19]2([CH3:20])[C:14](=[CH:15][C:16](=[O:27])[CH2:17][CH2:18]2)[CH2:13][CH2:12]3)[CH2:9][CH:8]=1)(=[O:3])[CH3:2].C([O-])(=[O:32])C.[NH4+].C(O)(=O)C.CC(C)=O>[Cl-].[Cl-].[Cl-].[Ti+3].O>[C:1]([O:4][CH2:5][C:6](=[O:32])[C:7]1[C@:24]2([CH3:25])[C@H:10]([C@H:11]3[C@:21]([OH:26])([CH2:22][CH2:23]2)[C@:19]2([CH3:20])[C:14](=[CH:15][C:16](=[O:27])[CH2:17][CH2:18]2)[CH2:13][CH2:12]3)[CH2:9][CH:8]=1)(=[O:3])[CH3:2]
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Komponenten

7

Edukt 4

HCID 176Acetic AcidHCID 180AcetoneHCID 517165Ammonium AcetateHCID 8674663521-Acetoxy-9alpha-hydroxy-20-hydroxyiminopregna-4,16-dien-3-one

Produkt 1

HCID 5717535021-Acetoxy-9alpha-hydroxypregna-4,16-diene-3,20-dione

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 10313229
titanium(III) trichloride
Katalysator
HCID 962WaterLösungsmittel

Versuchsvorschrift

A 15% (w/v) aqueous solution of titanium trichloride (4.1 ml) was added to a stirred suspension of 21-acetoxy-9α-hydroxy-20-hydroxyiminopregna-4,16-dien-3-one (0.50 g), ammonium acetate (1.5 g), acetic acid (10 ml) and acetone (3.75 ml) under nitrogen. After stirring at room temperature for 6 hours the reaction mixture was poured into water (30 ml) and extracted three times with diethyl ether. The combined organic layers were washed three times with 1N sodium hydroxide solution, then washed with aqueous sodium chloride solution and dried. The extract was evaporated under reduced pressure to afford the title compound as a foam.

Aufarbeitung

  1. extractionextracted three times with diethyl ether
  2. washThe combined organic layers were washed three times with 1N sodium hydroxide solution
  3. washwashed with aqueous sodium chloride solution
  4. customdried
  5. customThe extract was evaporated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-4953aa0ebe2c4c4bb0caf2db1a73b7aa
Quelldatensatz
uspto-grants-1993_03
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US05194602

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