Dexamethasone → Cortisol

HRID 1589956

Reaktionsgleichung

Reaktionsgleichung von HRID 1589956
[CH3:1][C@@:2]12[C@H:12]3[C@@H:13]([OH:26])[CH2:14][C@:15]4([CH3:25])[C@@:19]([OH:24])([C:20]([CH2:22][OH:23])=[O:21])[CH2:18][CH2:17][C@H:16]4[C@@H:11]3[CH2:10][CH2:9][C:8]1=[CH:7][C:5](=[O:6])[CH2:4][CH2:3]2.C[C@@:28]12[C@@:36](O)([C:37](CO)=[O:38])[CH2:35][CH2:34][C@H]1[C@@H]1CCC3[C@@](C)([C@H]1[C@@H](O)C2)C=CC(=O)C=3.C[C@H]1[C@](O)(C(CO)=O)[C@]2(C)[C@H]([C@H]3[C@](F)([C@@H](O)C2)[C@]2(C)C(=C[C:62](C=C2)=[O:63])CC3)C1.Cl(O)(=O)(=O)=[O:82]>ClCCl>[CH3:1][C@@:2]12[C@H:12]3[C@@H:13]([OH:26])[CH2:14][C@:15]4([CH3:25])[C@@:19]([OH:24])([C:20]([CH2:22][OH:23])=[O:21])[CH2:18][CH2:17][C@H:16]4[C@@H:11]3[CH2:10][CH2:9][C:8]1=[CH:7][C:5](=[O:6])[CH2:4][CH2:3]2.[CH:37]([CH:36]([CH2:35][CH3:34])[C:28]([O:63][CH3:62])=[O:82])=[O:38]

Komponenten

7

Edukt 4

HCID 5743DexamethasoneHCID 5754CortisolHCID 5755PrednisoloneHCID 24247Perchloric Acid

Produkt 2

HCID 5754CortisolHCID 15570303Methyl 2-formylbutanoate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

Hydrocortisone or prednisolone or dexamethasone or bethamethasone is reacted with an alkyl formylalkanoate in a solution of dichloromethane in the presence of catalytic amount of perchloric acid to produce the corresponding 17,21-carboxycyclic acetal pregnane derivatives, e.g., when hydrocortisone and methyl formylbutyrate are used the product is (IV) 11β-hydroxy-3,20-dioxo-17,21-(methoxycarbonyl-n-propyl) methylenedioxy-4-pregnene; when prednisolone and methyl formylacetate are used the product is (V) 11β-hydroxy-3,20-dioxo-17,21-(methoxycarbonylmethyl)methylenedioxy-1,4-pregnadiene.

Quellen und Nachweise

ORD-Eintrag
ord-24c5eaea82c048f8aa221ac72203ad67
Quelldatensatz
uspto-grants-1993_04
Patentnummer
US05200518

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