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

HRID 1589961

Reaktionsgleichung

Reaktionsgleichung von HRID 1589961
C[C@@:2]12[C@@:10](O)([C:11]([CH2:13]O)=[O:12])[CH2:9][CH2:8][C@H]1[C@@H]1CCC3[C@@](C)([C@H]1[C@@H](O)C2)C=CC(=O)C=3.C(NC(=O)[C@H](O)[C@]1(O)[C@]2(C)[C@H]([C@H]3[C@H]([C@@H:48]([OH:52])C2)[C@]2(C)C(=CC(=O)C=C2)CC3)CC1)CC.Cl(O)(=O)(=O)=[O:58]>>[C:11]([CH:10]([CH2:9][CH3:8])[C:2]([O:52][CH3:48])=[O:58])(=[O:12])[CH3:13]

Komponenten

4

Edukt 3

HCID 5755PrednisoloneHCID 24247Perchloric AcidHCID 13633149(20R)-21-(n-propylamino)-11beta,17, 20-trihydroxy-3,21-dioxo-1,4-pregnadiene2×

Produkt 1

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

Versuchsvorschrift

Prednisolone with 20-hydroxy and 20-carboxamide groups are known, e.g., (VI) (20R)-21-(n-propylamino)-11β,17, 20-trihydroxy-3,21-dioxo-1,4-pregnadiene; and (VI) is reacted with an alkyl acetylalkanoate or alkyl formylalkanoate in the presence of catalytic amount of perchloric acid to produce the corresponding 17,20-carboxycyclic acetal pregnane derivatives, e.g., when methyl acetylbutyrate is used the product is (VII) (20R)-21-(n-propylamino)-11β-hydroxy-3,21-dioxo-17,20-(methyl, methoxycarbony-n-propyl)methylenedioxy-1,4-pregnadiene.

Quellen und Nachweise

ORD-Eintrag
ord-b82907ef5780474b9ae8ccafd4809450
Quelldatensatz
uspto-grants-1993_04
Patentnummer
US05200518

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