Eli Lilly and Company

Nepera, Inc.

Laurence J Nummy

Gary A Koppel

Jun Li Wang

Sonia Rodriguez

Jon Charles Lorenz

Thomas Gabriel Tampone

Pengtao Zhang

Li Mei Zhang

Jolaine Savoie

Phouvieng Beyer

Joshua D Sieber

Kanwar Pal Singh Sidhu

Jason A Brazzillo

Magnus Eriksson

Zhulin Tan

Weitong Dong

The present invention relates to compounds of (II) and an acceptable salt or hydrate thereof method of making same.

Intermediate compounds and methods

Disclosed are compounds of the formula ##STR1## wherein R.sub.1 and R.sub.2 independently are H or C.sub.1-8 -alkyl or together are C.sub.2-7 -alkylene forming a ring with the connecting N-atom; X is CN, halo, C.sub.6-10 -arylsulfonyl, C.sub.6-10 -arylsulfinyloxy, C.sub.6-10 -aryloxy, C.sub.6-10 -arylthio or C.sub.1-8 -alkylsulfonyloxy or nitro, and Y is the anion of an acid having a pK.sub.a of about 3 or less. These compounds are intermediates in the preparation of 4-substituted pyridines.

Quaternary pyridine salts useful for preparation of 4-substituted

3-Hydroxymethyl-2-cephems are provided by (1) reacting a 2-halomethylcephem compound with a .gamma.-hydroxycarboxylic acid salt or a .delta.-hydroxycarboxylic acid salt and (2) reacting the novel .gamma. or .delta.-hydroxy esters thereby obtained with a protic acid. The 3-hydroxymethylcephems provided by the process of this invention are useful intermediates for the preparation of known cephalosporin antibiotics.

Process for preparation of 3-hydroxymethylcephems

Growing community of inventors

Newburgh, NY, United States of America

Laurence J Nummy