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

HRID 1589959

Reaktionsgleichung

Reaktionsgleichung von HRID 1589959
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.C(OC[C@@H](O)[C@]1(O)[C@]2(C)[C@H]([C@H]3[C@H]([C@@H](O)C2)[C@]2(C)C(=CC(=O)C=C2)CC3)CC1)(=[O:55])C.Cl(O)(=O)(=O)=O>>[C:20]([CH:19]([CH2:15][CH3:25])[C:18]([O:38][CH3:37])=[O:55])(=[O:21])[CH3:22]

Komponenten

5

Edukt 4

HCID 5754CortisolHCID 5755PrednisoloneHCID 24247Perchloric AcidHCID 1396238811beta,17,20beta,21-Tetrahydroxypregna-1,4-dien-3-one 21-Acetate2×

Produkt 1

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

Versuchsvorschrift

Hydrocortisone or prednisolone with 20-hydroxy and 21-acetoxy groups are known, e.g., (I) (20R)-21-acetoxy-11β, 17,20-trihydroxy-3-oxo-1,4-pregnadiene; and (I) is reacted with an alkyl acetylalkanoate 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 (II) (20R)-21-acetoxy-11β-hydroxy-3-oxo-17,20-(methyl,methoxycarbonyl-n-propyl)methylenedioxy-1,4-pregnadiene;

Quellen und Nachweise

ORD-Eintrag
ord-8ef4d1660fef44e1bc2033b1081f7dac
Quelldatensatz
uspto-grants-1993_04
Patentnummer
US05200518

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