Cefradine

Cefradine (INN) or cephradine (BAN) is a first generation cephalosporin antibiotic.

[citation needed] Birch reduction of D-α-phenylglycine led to diene (2).

This was N-protected using tert-butoxycarbonylazide and activated for amide formation via the mixed anhydride method using isobutylchloroformate to give 3.

Mixed anhydride 3 reacted readily with 7-aminodesacetoxycephalosporanic acid to give, after deblocking, cephradine (5).

The antibiotic is produced under many brand names across the world.

Cefradin synthesis: [ 2 ] [ 3 ] [ 4 ]