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Synthesis of 14C-labelled 7α-methoxycephalosporin derivative (CS-1170)

✍ Scribed by Hideo Nakao; Koichi Fujimoto; Hiroaki Yanagisawa

Publisher
John Wiley and Sons
Year
1978
Tongue
French
Weight
225 KB
Volume
15
Category
Article
ISSN
0022-2135

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✦ Synopsis

Sodium 7~-Cyanomethylthioacetamido-7a-14C-methoxy- 3-[ (1-methyl-1H-tetrazol-5-yl) thiomethyl) -3-cephem-4-carboxylate (CS-1170), a new cephamycin derivative was prepared for metabolic studies, The key reaction involves the methoxylation o f t'he diphenylmethyl 7-( 3 , 4 -d i -~-b u t y l -4 -o x 0 -2 , 5 -c y c l o h e x a d i e n -l -y l e n ) methylimino-3-((l-methyl-1H-tetrazol-5-yl)thiomethyl)-3-cephem-4-carboxylate (I) with 14CH30H to diphenylmethyl 7 ~-( 3 , 5 -d i -t ~t -b u t y l -4 -h y d r o x y b e n z y l i d e n e a r n i n o ) - 7a-14C-me thoxy-3-( ( 1 -me thy 1-1H-t e t r az o 1-5 -y 1 ) t hi omethyl)-3-cephem-4-carboxylate (11). Cleavage o f the Schiff base, acylation followed by hydrolysis produced the desired radioactive drug. The overall radiochemical yield was 14$, at 8 specific activity o f 12.7 uCi/mg.

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