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Carbon‐14 labeling of Saxagliptin (BMS‐477118)
Author(s) -
Cao Kai,
Bonacorsi Samuel J.,
Balasubramanian Balu,
Hanson Ronald L.,
Manchand Percy,
Godfrey Jollie D.,
Fox Rita,
Christopher Lisa J.,
Su Hong,
Iyer Ramaswamy
Publication year - 2007
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.1450
Subject(s) - chemistry , oxalyl chloride , yield (engineering) , sequence (biology) , bromide , saxagliptin , chloride , glycine , decarboxylation , ferrocene , combinatorial chemistry , stereochemistry , medicinal chemistry , organic chemistry , catalysis , amino acid , electrochemistry , biochemistry , medicine , materials science , metformin , electrode , sitagliptin , metallurgy , diabetes mellitus , endocrinology
An efficient synthesis of carbon‐14‐labeled Saxagliptin (BMS‐477118) is described. Initial synthesis of the key radiolabeled intermediate ( S )‐ N ‐Boc‐2‐(3′‐hydroxyadamantyl)glycine 2a utilized adamantanemethanol in a 10‐step sequence. To shorten the sequence, 1‐adamantylzinc bromide was reacted with ethyl [1, 2‐ 14 C]oxalyl chloride catalyzed by [1,1′‐bis(diphenylphosphino)ferrocene]dichloropalladium (II). In five steps, 2b was synthesized in an overall yield of 20% based on ethyl [1, 2‐ 14 C]oxalyl chloride. Compound 2b was subsequently converted to [ 14 C] BMS‐477118 in a short sequence. Copyright © 2007 John Wiley & Sons, Ltd.