Acetone → Anecortave Acetate

HRID 65344

Reaktionsgleichung

Reaktionsgleichung von HRID 65344
[OH:1][C@:2]1([C@:28]2([CH3:29])[C@H:14]([C@H:15]3[C:25](=[CH:26][CH2:27]2)[C@:23]2([CH3:24])[C:18](=[CH:19][C:20](=[O:30])[CH2:21][CH2:22]2)[CH2:17][CH2:16]3)[CH2:13][CH2:12]1)[C:3]([O:5]C1C=CC=CC=1)=[CH2:4].P([O-])([O-])([O-])=O.[K+].[K+].[K+].OOS([O-])=O.[K+].[OH-:45].[K+].C[C:48]([CH3:50])=[O:49]>O.C1(C)C=CC=CC=1.C(Cl)Cl>[OH:1][C@:2]1([C@:28]2([CH3:29])[C@H:14]([C@H:15]3[C:25](=[CH:26][CH2:27]2)[C@:23]2([CH3:24])[C:18](=[CH:19][C:20](=[O:30])[CH2:21][CH2:22]2)[CH2:17][CH2:16]3)[CH2:13][CH2:12]1)[C:3](=[O:4])[CH2:5][O:49][C:48](=[O:45])[CH3:50]

Komponenten

8

Edukt 5

HCID 180Acetone2×HCID 14797Potassium HydroxideHCID 62657Potassium Phosphate, TribasicHCID 1382382517alpha-Hydroxy-20-phenoxypregna-4,9(11),20-trien-3-oneHCID 23707502Potassium hydroxy sulfite

Produkt 1

HCID 111332Anecortave Acetate

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 21877217Toluene methylene chlorideLösungsmittel

Reaktionsbedingungen

Temperatur
15 °C

Versuchsvorschrift

17α-hydroxy-20-phenoxypregna-4,9(11),20-trien-3-one (4.05 grams, 10 mmoles) is slurried with 210 ml of an aqueous pH 8 potassium phosphate buffer (0.5M in PO4 ≡), 20 ml of acetone, 40 ml of toluene/methylene chloride (3:2) and n-tetrabutylammonium bromide is (0.645 grams, 2.0 mmole) added. The pH is adjusted to 7.0 to 8.0 and the mixture cooled to 15° C. and an OXONE® solution is (18.4 gms, 30 mmoles dissolved in 65 ml of water) added dropwise by an addition funnel while stirring and maintaining pH at 7.0 to 8.0 by addition of a 30% potassium hydroxide solution. The reaction is worked up by separating the layers and replacing the organic solvent with toluene to a volume of 100 ml so as to remove water. After cooling to 10° C., 3 ml of glacial acetic acid is added. The product is isolated by replacing the toluene with acetone and filtering to obtain 3.12 g of 17α-hydroxy-21-acetoxypregna-4,9(11)-diene-3,20-dione.

Aufarbeitung

  1. additionadded
  2. additionadded dropwise by an addition funnel
  3. temperaturemaintaining pH at 7.0 to 8.0
  4. customby separating the layers
  5. customto remove water
  6. temperatureAfter cooling to 10° C.
  7. addition3 ml of glacial acetic acid is added
  8. customThe product is isolated
  9. filtrationfiltering

Quellen und Nachweise

ORD-Eintrag
ord-a9ec3ad44eae4e0c8fd779ec69e81f7c
Quelldatensatz
uspto-grants-1986_09
Patentnummer
US04613463

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