Boron trifluoride → 7-Aminodeacetoxycephalosporanic acid

Participants

Reaction Steps

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).

Provenance & Evidence