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Synthesis of [13C4]Baraclude® (entecavir)

✍ Scribed by Scott B. Tran; Ihoezo V. Ekhato; J. Kent Rinehart

Publisher
John Wiley and Sons
Year
2009
Tongue
French
Weight
132 KB
Volume
52
Category
Article
ISSN
0022-2135

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✦ Synopsis

Abstract

Entecavir, labeled as 1H‐[^13^C~4~]purin‐6(9H)‐one, was prepared from commercially available [^13^C]guanidine HCl, 1 and diethyl [1,2,3‐^13^C~3~]malonate, 2. The reagents were condensed together to give 2‐amino‐4,6‐dichloro[2,4,5,6‐^13^C~4~]pyrimidine 3, which in turn was coupled to an optically active amino cyclopentanol derivative, 9. A further sequence of eight reaction steps completed the constructions of the purine ring system and the exocyclic olefin attachment on the cyclic pentyl portion, 18. The removal of the methoxide and benzyl protecting groups gave [^13^C~4~]entecavir, 20 in an overall yield of 6.8%. The chemical purity of the title compound was determined by HPLC to be 99.23%. The percent isotopic [^13^C~4~] abundance was found by mass spectral analysis to be 96.7%. No detectable level of the unlabeled entecavir was found by LC‐MS analysis. Copyright © 2009 John Wiley & Sons, Ltd.

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