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M+4 stable isotope labeling of levovirin and M+7 and carbon-14 labeling of levovirin valinate pro-drug

✍ Scribed by Steve A. de Keczer; Mohammad R. Masjedizadeh; Shao-Yong Wu; Teresa Lara-Jaime; Kate Comstock; Charles Dvorak; Yu-Ying Liu; Walter Berger


Publisher
John Wiley and Sons
Year
2006
Tongue
French
Weight
177 KB
Volume
49
Category
Article
ISSN
0022-2135

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✦ Synopsis


Abstract

[M+4]‐labeled levovirin 5 (231 mg) was synthesized as an MS reference compound from [M+4] triazole ester 2. [M+7]‐labeled levovirin valinate 6 (127 mg) was synthesized as a comparison MS reference compound from [M+6] triazole ester 3. [^14^C]‐Levovirin 7 and [^14^C]‐levovirin valinate 8 were synthesized to support metabolism studies. The synthesis of 7 was accomplished in 33% overall yield (35.4 mCi, 57 mCi/mmol) from Ba^14^CO~3~ and 8 was synthesized in 41% yield (12.5 mCi, 57 mCi/mmol) from 7. An efficient metallation/carbonation reaction was developed to synthesize [^14^C]‐triazole ester 4. Copyright © 2006 John Wiley & Sons, Ltd.


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