Hydrochloric Acid → 9,21-Dihydroxypregn-4-ene-3,20-dione

HRID 1613975Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1613975
Cl.C(N/[C:5](=[C:8]1/[CH2:9][CH2:10][C@@H:11]2[C@:25]/1([CH3:26])[CH2:24][CH2:23][C@@:22]1([OH:27])[C@H:12]2[CH2:13][CH:14]=[C:15]2[C@:20]1([CH3:21])[CH2:19][CH2:18][C:17]([O:28]C)=[CH:16]2)/[CH2:6][OH:7])=O.C[OH:31]>>[OH:27][C@:22]12[CH2:23][CH2:24][C@@:25]3([CH3:26])[C@@H:11]([CH2:10][CH2:9][C@@H:8]3[C:5](=[O:31])[CH2:6][OH:7])[C@@H:12]1[CH2:13][CH2:14][C:15]1[C@:20]2([CH3:21])[CH2:19][CH2:18][C:17](=[O:28])[CH:16]=1

Komponenten

4

Edukt 3

HCID 313Hydrochloric AcidHCID 887MethanolHCID 86746638(20Z)-20-Formamido-3-methoxypregna-3,5,17(20)-triene-9alpha,21-diol

Produkt 1

HCID 571918849,21-Dihydroxypregn-4-ene-3,20-dione

Versuchsvorschrift

Aqueous 5N hydrochloric acid (1 ml) was added to a stirred solution of (20Z)-20-formamido-3-methoxypregna-3,5,17(20)-triene-9α,21-diol (70 mg) in methanol (4 ml). The reaction mixture was stirred at room temperature for 1 hour, then extracted with ethyl acetate. The organic extract was washed with an aqueous sodium bicarbonate solution, twice with water, dried and concentrated under reduced pressure to afford the title compound.

Aufarbeitung

  1. extractionextracted with ethyl acetate
  2. extractionThe organic extract
  3. washwas washed with an aqueous sodium bicarbonate solution, twice with water
  4. customdried
  5. concentrationconcentrated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-dde6bdac6ce64edeb88aad39c90732a4
Quelldatensatz
uspto-grants-1993_03
Patentnummer
US05194602

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