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Synthesis of carbon-14 labelled antimicrobial agents. II. Synthesis of apalcillin-14C sodium

✍ Scribed by Akira Yoshitake; Takeshi Kamada; Hideyuki Gomi; Iwao Nakatsuka

Publisher
John Wiley and Sons
Year
1981
Tongue
French
Weight
284 KB
Volume
18
Category
Article
ISSN
0022-2135

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✦ Synopsis

Abstract

Sodium 6‐[ (R)‐2‐(4‐hydroxy‐1,5‐naphthyridine‐4‐^14^C‐3‐carboxy‐^14^C‐amido)‐2‐phenylacetamido]penicillanate (apalcillin‐^14^C sodium) (1) was synthesized for use in metabolic studies. Reaction of ethyl malonate‐1‐^14^C (2) with ethyl orthoformate in the presence of zinc chloride gave ethyl ethoxymethylenemalonatel‐^14^C (3), which was condensed with 3‐aminopyridine to give the aminopyridylacrylate‐^14^C (4). Cyclization of 4 in boiling. Dowtherm A followed by hydrolysis of the resulting ester gave 4‐hydroxy‐1, 5‐naphthyridine‐4‐^14^C‐3‐carboxylic‐^14^C acid (5). Condensation of 5 with 6‐[ (R)‐2‐amino‐2‐phenylacetamido]penicillanic acid by the activated ester method yielded apalcillin‐^14^C triethylamonium (7), which in turn was treated with sodium 2‐ethylhexanoate, giving apalcillin‐^14^C sodium (1) in the overall yield of 17% based on 2.

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