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Substances naturelles marquées au carbone 14 I. Synthèse d'un isomère de la triacanthine: La N 6 ‐[méthyl‐3 butényl‐2 ( 14 C‐1)] adénine
Author(s) -
Herbert Michel,
Pichat Louis
Publication year - 1971
Publication title -
journal of labelled compounds
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.432
H-Index - 47
eISSN - 1099-1344
pISSN - 0022-2135
DOI - 10.1002/jlcr.2590070318
Subject(s) - phthalimide , chemistry , medicinal chemistry , diazomethane , bromide , yield (engineering) , organic chemistry , materials science , metallurgy
Abstract Carbonation by 14 CO 2 of the Grignard derivative from 1‐isobutenyl bromide gave with a yield of 94% 3,3‐dimethylacrylic acid 14 C‐1 which was esterified by diazomethane into methyl 3,3‐dimethylacrylate 14 C‐1. The latter was reduced by LiAlH 4 + AlCl 3 into 3‐methyl‐2‐buten‐1‐ol 14 C‐1 then converted to l‐bromo‐3‐methyl‐2‐butene 14 C‐1 by treatment with PBr 3 . N‐(3‐methyl‐2‐butenyl) phthalimide 14 C‐1 was obtained by action of potassium phthalimide on the bromide in D. M. F. The liberation of 3,3‐dimethylallylamine 14 C‐1 and its condensation with 6‐chloropurine led to N 6 ‐[3‐methyl‐2‐butenyl( 14 C‐1)] adenine with a radioactive overall yield of 14% based on Ba 14 CO 3 , specific activity: 38 mCi/mM.