Original scientific paper

Application of 4-Chlorobutyryl Group as Amino Protective Group in the Synthesis of 7-(D-2-Amino-2-phenylacetamido)-3-methyl-3-cephem-4-carboxylic Acid (Cephalexin)

Z. Mandić ; Research Institute PLIVA, Zagreb, Croatia, Yugoslavia
J. J. Herak ; Research Institute PLIVA, Zagreb, Croatia, Yugoslavia
M. Tomić ; Research Institute PLIVA, Zagreb, Croatia, Yugoslavia
B. Vranešić ; Research Institute PLIVA, Zagreb, Croatia, Yugoslavia
M. Kovačević ; Research Institute PLIVA, Zagreb, Croatia, Yugoslavia
B. Gašpert ; Research Institute PLIVA, Zagreb, Croatia, Yugoslavia

Abstract

4-Chlorobutyryl group was used as amino protective group
for n(-)-alpha-phenylglycine (I). N-Hydroxysuccinimide ester III
was prepared in high yield but partly racemic. Reaction of III
or IV with V afforded epimeric mixtures of N,0-protected cephalexins
(VI), which can be separated by crystallisation. The 4-chlorobutyryl
group in VII was removed under very mild conditions
giving cephalexin (IX) in good yield and purity.

Keywords

Hrčak ID:

194437

URI

https://hrcak.srce.hr/194437

Publication date:

15.3.1981.

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