Synthesis of (5‐methyl‐2‐oxo‐1,3‐dioxol‐4‐YL)methyl 7‐[D‐O‐(L‐alanyl)[β‐¹⁴C]mandelamido]‐3‐[[(5‐methyl‐1,3,4‐thiadiazol‐2‐YL)thio]methyl]‐3‐cephem‐4‐carboxylate and its active compound

Abstract

5-Methyl-2-oxo-l,3-dioxol-4-yl)methyl 7-1 D-0-(L-alanyl) [B-l4C]mandelamido]-3-[ [ (5-methyl-l,3 ,4-thiadiazol-2-yl) thio ]methyl]-3-cephem-4carboxylate (14C-KY-1 09) and its parent drug (1h-KY-087) were synthesized from D-(-)-mandelic-&lh acid prepared by optical resolution of DL-(2)-mandeli~-B-'~C acid. KY-087 and 49.6% for '4C-Icp-109, based on D-(-)-mandelic-f3-l4C acid. Both the products had radiochemical purities greater than 97% as measured by TLC. The overall radiochemical yields were 16.2% f o r 14C-Key Words: (5-methyl-2-oxo-l,3-dioxol-4-yl )methyl 7-[D-O-(L-alanyl) [ B-' 4C]mandelamido 1-3-[ [ (5-methyl-l,3,4-thiadiazol-2-yl) thio ]methyl]-3-cephem-4carboxylate, 7-(D-[ B-14Clmandelamido)-3-[ [ (5-methyl-l,3,4-thiadiazol-2-y1)thiol methyl 1-3-cephem-4-carboxylic acid, [ 4C ]cephalosporin analogue.