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Syntheses of [6‐ 14 C] and [5‐ carboxy , 6‐ 14 C 2 ]nitrendipine
Author(s) -
Maul W.,
Scherling D.
Publication year - 1989
Publication title -
journal of labelled compounds and radiopharmaceuticals
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.432
H-Index - 47
eISSN - 1099-1344
pISSN - 0362-4803
DOI - 10.1002/jlcr.2580270413
Subject(s) - chemistry , nitrendipine , methanol , ethyl acetoacetate , meldrum's acid , ammonia , chloride , organic chemistry , barium carbonate , boiling , barium chloride , medicinal chemistry , toluene , catalysis , raw material , calcium
[6‐ 14 C]Nitrendipine synthesis started from barium[ 14 ]carbonate, which was converted to [1‐ 14 C]acetyl chloride. The acid chloride was condensed with Meldrum's acid (2,2‐dimethyl‐1,3‐dioxane‐4,6‐dione). The resulting intermediate was treated with boiling methanol to give methyl [3‐ 14 C]acetoacetate. The reaction with gaseous ammonia in toluene yielded the corresponding methyl 3‐amino[3‐ 14 C]crotonate which was condensed with ethyl 2‐(3‐nitro‐benzylidene) acetoacetate to obtain [6–14C]nitrendipine. [5‐ carboxy , 6‐ 14 C 2 ]Nitrendipine was synthesized by an analogous procedure starting from methyl [1,3‐ 14 C 2 ]acetoacetate.