An alternative and robust synthesis of [13C4]Baraclude® (entecavir)
| Autor: | Richard C. Burrell, Samuel J. Bonacorsi, John A. Easter |
|---|---|
| Rok vydání: | 2013 |
| Předmět: |
Hydrochloride
Organic Chemistry Carbon-13 Epoxide Entecavir Biochemistry High-performance liquid chromatography Medicinal chemistry Analytical Chemistry chemistry.chemical_compound Malonate chemistry Yield (chemistry) Drug Discovery medicine Organic chemistry Radiology Nuclear Medicine and imaging Guanidine Spectroscopy medicine.drug |
| Zdroj: | Journal of Labelled Compounds and Radiopharmaceuticals. 56:632-636 |
| ISSN: | 0362-4803 |
| Popis: | Stable isotope-labeled [(13) C4 ]entecavir (1) was prepared in 11 steps. Commercially available [(13) C]guanidine hydrochloride and diethyl[1,2,3-(13) C3 ]malonate were condensed to yield 2-amino[2,4,5,6-(13) C4 ]pyrimidine-4,6-diol (8). This was converted to the desired purine (7) in five steps. Introduction of the chiral epoxide was followed by subsequent deprotection to give [(13) C4 ]entecavir (1), in an overall yield of 5.7% from labeled precursors. The chemical purity of the title compound was determined to be >99% by HPLC. The isotopic distribution was determined by mass spectrometry to be 282[M + 4], 98.4%; 281[M + 3], 1.6%; and 278[M + 0] |
| Databáze: | OpenAIRE |
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