Rapid, mild method for phosphonate diester hydrolysis: development of a one-pot synthesis of tenofovir disoproxil fumarate from tenofovir diethyl ester
| Autor: | Joseph M. Fortunak, David H. Brown Ripin, Jack Melton, Stephen R. Houghton, Christopher N. Boddy |
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| Rok vydání: | 2010 |
| Předmět: |
Tenofovir
Organic Chemistry Diethyl ester One-pot synthesis Human immunodeficiency virus (HIV) virus diseases Alkylation medicine.disease_cause Biochemistry Phosphonate Combinatorial chemistry Chemical synthesis chemistry.chemical_compound Hydrolysis chemistry immune system diseases Drug Discovery medicine Organic chemistry medicine.drug |
| Zdroj: | Tetrahedron. 66:8137-8144 |
| ISSN: | 0040-4020 |
| DOI: | 10.1016/j.tet.2010.08.037 |
| Popis: | A rapid, low temperature hydrolysis of tenofovir diethyl ester mediated by TMSCl and NaBr was identified and demonstrated to be superior to the current production method, TMSBr-mediated hydrolysis. This mild phosphonate ester hydrolysis was then coupled to alkylation of the phosphonic acid, providing a one-pot procedure for formation of tenofovir disoproxil from tenofovir diethyl ester. The hydrolytic conditions developed here dramatically improve the synthesis of tenofovir disoproxyl and will lead to lower cost HIV/AIDS treatment in the developing world. |
| Databáze: | OpenAIRE |
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