Acetone → 21-Desacetoxy-21-Chloro Anecortave

HRID 2198390Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2198390
[Cl:1][CH:2]=[C:3]([O:25]C)[C@:4]1([OH:24])[C@:21]2([CH3:22])[C@H:7]([C@H:8]3[C:18](=[CH:19][CH2:20]2)[C@:16]2([CH3:17])[C:11](=[CH:12][C:13](=[O:23])[CH2:14][CH2:15]2)[CH2:10][CH2:9]3)[CH2:6][CH2:5]1.C1COCC1.CC(C)=O.Cl>CCCCCC.CO>[Cl:1][CH2:2][C:3](=[O:25])[C@:4]1([OH:24])[C@:21]2([CH3:22])[C@H:7]([C@H:8]3[C:18](=[CH:19][CH2:20]2)[C@:16]2([CH3:17])[C:11](=[CH:12][C:13](=[O:23])[CH2:14][CH2:15]2)[CH2:10][CH2:9]3)[CH2:6][CH2:5]1

Komponenten

7

Edukt 4

HCID 180AcetoneHCID 313Hydrochloric AcidHCID 8028TetrahydrofuranHCID 8673851121-Chloro-17alpha-hydroxy-20-methoxypregna-4,9(11),20-trien-3-one

Produkt 1

HCID 1303765421-Desacetoxy-21-Chloro Anecortave

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 887MethanolLösungsmittelHCID 8058HexaneLösungsmittel

Versuchsvorschrift

21-Chloro-17α-hydroxy-20-methoxypregna-4,9(11),20-trien-3-one (IX, Example 4, 1.0 g), THF (4 ml), acetone (4.9 ml), and methanol (1.4 ml) are mixed. Aqueous hydrochloric acid (6 N, 0.44 ml) is added and the resulting slurry heated at 40° for 1.5 hours. The mixture is cooled to 20°-25° and diluted with hexane (3 ml). The solids are isolated by filtration and washed with hexane/ethyl acetate (85/15, 13 ml) to give the title compound.

Aufarbeitung

  1. temperaturethe resulting slurry heated at 40° for 1.5 hours
  2. temperatureThe mixture is cooled to 20°-25°
  3. customThe solids are isolated by filtration
  4. washwashed with hexane/ethyl acetate (85/15, 13 ml)

Quellen und Nachweise

ORD-Eintrag
ord-1dd7ff70ebe147bba322a69581e40cf3
Quelldatensatz
uspto-grants-1982_11
Patentnummer
US04357279

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