Cortisol → Butanoic acid, 2-ethyl-3-oxo-, methyl ester

HRID 1589960

Reaktionsgleichung

Reaktionsgleichung von HRID 1589960
C[C@@]12[C@H]3[C@@H](O)C[C@:15]4([CH3:25])[C@@:19](O)([C:20]([CH2:22]O)=[O:21])[CH2:18]C[C@H]4[C@@H]3CCC1=CC(=O)CC2.C[C@@]12[C@@](O)([C:37](CO)=[O:38])CC[C@H]1[C@@H]1CCC3[C@@](C)([C@H]1[C@@H](O)C2)C=CC(=O)C=3.[OH:53][C@H]1C[C@@]2(C)[C@@H](CC[C@]2(OC(=O)C)C(=O)COC(=O)C)[C@H]2[C@H]1[C@]1(C)C(CC2)=CC(=O)C=C1.Cl(O)(=O)(=O)=O>>[C:20]([CH:19]([CH2:15][CH3:25])[C:18]([O:38][CH3:37])=[O:53])(=[O:21])[CH3:22]

Komponenten

5

Edukt 4

HCID 5754CortisolHCID 5755PrednisoloneHCID 24247Perchloric AcidHCID 14233395Prednisolone 17,21-diacetate2×

Produkt 1

HCID 103534Butanoic acid, 2-ethyl-3-oxo-, methyl ester

Versuchsvorschrift

Hydrocortisone or prednisolone with 20-hydroxy and 20-carboxy groups are known, e.g., (III) methyl (20R)-11β,17, 20-trihydroxy-3-oxo-1,4-pregnadien-21-oate; and (III) is reacted with an alkyl acetylalkanoate or alkyl formylalkanoate in the presence of perchloric acid to produce the corresponding 17,20-carboxycyclic acetal pregnane derivatives, e.g., when methyl acetylbutyrate is used the product is (IV) methyl (20R)-11β-hydroxy-3-oxo-17,20-(methyl,methoxycarbonyl-n-propyl)methylenedioxy-1,4-pregnadien-21-oate; when methyl formylformate is used the product is (V) methyl (20R)-11β-hydroxy-3-oxo-17,20-(methoxycarbonyl)methylenedioxy-1,4-pregnadien-21-oate;

Quellen und Nachweise

ORD-Eintrag
ord-7afdfbdc1cd74a85882ac9fab4bd0b69
Quelldatensatz
uspto-grants-1993_04
Patentnummer
US05200518

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