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An efficient synthesis of [ring‐ 14 C]‐L‐tyrosine from [U‐ 14 C]‐phenol
Author(s) -
Kendall John T.
Publication year - 2000
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/(sici)1099-1344(200004)43:5<505::aid-jlcr336>3.0.co;2-0
Subject(s) - chemistry , phenol , ring (chemistry) , tyrosine , stereochemistry , organic chemistry , biochemistry
The title compound was prepared in good overall yield and high enantiopurity via a five step route beginning with [U‐ 14 C]‐phenol, 4 . Benzyl ether 5 was prepared from 4 under standard conditions and underwent selective iodination at the 4‐position in the presence of iodine and mercuric oxide. Palladium catalysed cross coupling of the resulting aryl iodide 6 and the organozinc intermediate derived from N‐ tert ‐butoxycarbonyl‐3‐iodo‐alanine methyl ester, 7 , proceeded smoothly to give 8 . Debenzylation and acid hydrolysis afforded the deprotected amino acid as the hydrochloride salt. Purification (flash chromatography) was necessary in only two of the five steps in the synthesis. Copyright © 2000 John Wiley & Sons, Ltd.