Collect. Czech. Chem. Commun. 1999, 64, 2035-2043

Coupling of Steroid O-(Carboxymethyl)oxime Derivatives with Single-Protected α,ω-Diaminoalkanes

Vladimír Pouzar*, Ivan Černý and Pavel Drašar

Institute of Organic Chemistry and Biochemistry, Academy of Sciences of the Czech Republic, Flemingovo nám. 2, 166 10 Prague 6, Czech Republic


New approach to the synthesis of steroid oximes bearing O-substituents with terminal amino groups was described. The easily accessible steroid O-(carboxymethyl)oximes were reacted with single-protected Boc-α,ω-diaminoalkanes to give corresponding amide intermediates. From them the Boc protecting groups were cleaved with trifluoroacetic acid to afford the desired steroid derivatives with terminal amino groups. The procedure was succesfully tested on steroids with O-(carboxymethyl)oxime group in positions 7 and 17. The decomposition of target products was observed during deprotection of substituted 19-oximes.

Keywords: Steroids; O-Alkyloximes; Amides; Fluoroimmunoassays; Haptens.