Boron trifluoride → 7-Aminodeacetoxycephalosporanic acid

HRID 67722

Reaktionsgleichung

Reaktionsgleichung von HRID 67722
CC(OCC1CS[C@@H]2CC(=O)N2C=1C(O)=O)=O.CC(O[CH2:22][C:23]1[CH2:32][S:31][C@@H:26]2[C@H:27]([NH2:30])[C:28](=[O:29])[N:25]2[C:24]=1[C:33]([OH:35])=[O:34])=O.C([SiH](CC)CC)C.B(F)(F)F>FC(F)(F)C(O)=O>[CH3:22][C:23]1[CH2:32][S:31][C@@H:26]2[C@H:27]([NH2:30])[C:28](=[O:29])[N:25]2[C:24]=1[C:33]([OH:35])=[O:34]

Komponenten

6

Edukt 4

HCID 6356Boron trifluorideHCID 12052TriethylsilaneHCID 4413287-Aminocephalosporanic acidHCID 12302722Cephalosporanic Acid

Produkt 1

HCID 334987-Aminodeacetoxycephalosporanic acid

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6422Trifluoroacetic acidLösungsmittel

Versuchsvorschrift

7-Amino- and 7-(N,N-disubstituted)aminocephalosporanic acids are converted to the corresponding 3-methyl-3-cephem-4-carboxylic acids by reacting the cephalosporanic acid with a tri(C1 -C6 alkyl)silane in the presence of an organic acid having a pKa of <1.5 and a Lewis acid. For example, 7-aminocephalosporanic acid (7-ACA) is reacted with triethylsilane in trifluoroacetic acid in the presence of boron trifluoride to provide 7-aminodesacetoxycephalosporanic acid (7-ADCA).

Quellen und Nachweise

ORD-Eintrag
ord-5839f80241c9416d8fedb469604d03a4
Quelldatensatz
uspto-grants-1982_08
Patentnummer
US04346219

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