Rapid, mild method for phosphonate diester hydrolysis: development of a one-pot synthesis of tenofovir disoproxil fumarate from tenofovir diethyl ester
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, providin...
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| Veröffentlicht in: | Tetrahedron 2010-10, Vol.66 (41), p.8137-8144 |
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| container_end_page | 8144 |
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| container_issue | 41 |
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| container_title | Tetrahedron |
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| creator | Houghton, Stephen R. Melton, Jack Fortunak, Joseph Brown Ripin, David H. Boddy, Christopher N. |
| description | 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.
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| doi_str_mv | 10.1016/j.tet.2010.08.037 |
| format | Article |
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| fulltext | fulltext |
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| ispartof | Tetrahedron, 2010-10, Vol.66 (41), p.8137-8144 |
| issn | 0040-4020 1464-5416 |
| language | eng |
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| source | Elsevier ScienceDirect Journals |
| subjects | Chemistry Esters Exact sciences and technology Heterocyclic compounds Heterocyclic compounds with several n hetero atoms in the same ring, in separated rings or in fused rings HIV Hydrolysis Joining Organic chemistry Phosphoate ester hydrolysis Phosphonates Preparations and properties Production methods Synthesis (chemistry) Tenofovir Tetrahedrons TMSBr |
| title | Rapid, mild method for phosphonate diester hydrolysis: development of a one-pot synthesis of tenofovir disoproxil fumarate from tenofovir diethyl ester |
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