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Synthesis of [14C]ABT-770, matrix metalloproteinase inhibitor (MMPI), labelled in the phenoxy ring

✍ Scribed by Shirish N. Raja

Publisher
John Wiley and Sons
Year
2003
Tongue
French
Weight
120 KB
Volume
46
Category
Article
ISSN
0022-2135

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✦ Synopsis

Abstract

The MMPI [^14^C]ABT‐770 (1), N‐[(1S)‐1‐[(4,4‐Dimethyl‐2,5‐dioxo‐1‐imi‐dazolidinyl)methyl]]‐2‐[[4′‐(trifluoromethoxy)[1,1′‐biphenyl]‐4‐yl]oxy]ethyl]‐N‐hydroxyformamide was synthesized in 8 steps using 4‐bromophenol‐UL‐^14^C (10) as a starting material. The Carbon‐14 label was introduced in one of the metabolically stable biphenyl rings. The key sequence of the synthesis was a three‐step one‐pot reaction in which the hydantoin moiety was introduced, the imine oxidized and further hydrolyzed to get the penultimate precursor to [^14^C]ABT‐770 (1) in 56% yield. Copyright © 2003 John Wiley & Sons, Ltd.

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