Halogenating reagents
AssigneeEli Lilly and Company
InventorsLowell D. Hatfield, Larry C. Blaszczak, Jack W. Fisher
Life of this patent
Estimating the term…
Abstract
Novel halogenating agents are derived from triaryl phosphites and chlorine or bromine. They are useful in converting 7-acylamino-3-hydroxy-3-cephem compounds to 7-acylamino-3-halo-3-cephems and the corresponding C-7 imino halide cephem derivatives.
Claims15
A halogenating compound of the general formula ##STR8## which is the kinetically controlled product of the reaction of equivalent amounts of a triaryl phosphite of the formula ##STR9## and chlorine or bromine in a substantially anhydrous inert organic solvent wherein in the above formulas Z is hydrogen, halo, C.sub.1 -C.sub.4 alkyl or C.sub.1 -C.sub.4 alkoxy, and X is Cl or Br.
A compound having the empirical formula ##STR10## which (a) has a .sup.31 P nuclear magnetic resonance signal in methylene chloride at -3.7 ppm relative to that of phosphoric acid;
- (b) has in, methylene chloride, an infrared spectrum which exhibits the following characteristic absorptions:
- 1120-1190 (very strong), 1070 (very strong), 1035 (strong), 1010 (very strong), 990 (very strong), 640 (medium), 625 (medium), 580 (weak), 510 (strong) and 465 (weak);
- (c) reacts with water to give HCl and triphenyl phosphate;
- and
- (d) reacts with n-butanol to give HCl, n-butyl chloride, and triphenyl phosphate.
A compound having the empirical formula ##STR11## which has a .sup.31 P nuclear magnetic resonance signal in methylene chloride at -3.7 ppm relative to that of phosphoric acid.
Dependencies are inferred from the claim text.