Dexamethasone → Dexamethasone 9,11-epoxide

HRID 370413

Reaktionsgleichung

Reaktionsgleichung von HRID 370413
[CH3:1][C@H:2]1[C@:19]([OH:24])([C:20]([CH2:22][OH:23])=[O:21])[C@:18]2([CH3:25])[C@H:4]([C@H:5]3[C@:15](F)([C@@H:16]([OH:26])[CH2:17]2)[C@:14]2([CH3:28])[C:8](=[CH:9][C:10]([CH:12]=[CH:13]2)=[O:11])[CH2:7][CH2:6]3)[CH2:3]1.O[C@@]1([C@]2(C)[C@H]([C@H]3C(=CC2)[C@]2(C)C(=CC(=O)C=C2)CC3)CC1=C)C(=O)C>>[O:26]1[C@@H:16]2[C@:15]31[C@H:5]([C@H:4]1[C@:18]([CH3:25])([CH2:17]2)[C@@:19]([OH:24])([C:20](=[O:21])[CH2:22][OH:23])[C@H:2]([CH3:1])[CH2:3]1)[CH2:6][CH2:7][C:8]1[C@:14]3([CH3:28])[CH:13]=[CH:12][C:10](=[O:11])[CH:9]=1

Komponenten

3

Edukt 2

HCID 5743DexamethasoneHCID 1357883717beta-Hydroxy-16-methylenepregna-1,4,9(11)-triene-3,20-dione

Produkt 1

HCID 11143226Dexamethasone 9,11-epoxide

Versuchsvorschrift

Dexamethasone (9α-fluoro-11β,17α,21-trihydroxy-16α-methylpregna-1,4-diene-3,20-dione) can also be prepared from 17β-hydroxy-16-methylenepregna-1,4,9(11)-triene-3,20-dione by first transforming it to 17α,21-dihydroxy-16-methylenepregna-1,4,9(11)-triene-3,20-dione 21-acetate as described above and next transforming it to 17α,21-dihydroxy-16α-methylpregna-1,4,9(11)-triene-3,20-dione 21-acetate by the process of U.S. Pat. No. 3,130,209. 17α,21-Dihydroxy-16α-methylpregna-1,4,9(11)-triene-3,20-dione 21-acetate is then epoxidized by means well known to those skilled in the art, see for example U.S. Pat. No. 3,980,778, Examples 2 and 7 to produce 9β,11β-epoxy-17α,21-dihydroxy-16α-methylpregna-1,4-diene-3,20-dione which is transformed to dexamethasone 21-acetate by the process of U.S. Pat. No. 3,007,932, Example 2.

Quellen und Nachweise

ORD-Eintrag
ord-bb5fd5e14b334bf9a93e97cb5597a1fa
Quelldatensatz
uspto-grants-1985_07
Patentnummer
US04526720

Verknüpfte Notizen

Wird geladen…