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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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| Authors: | Stephen R. Houghton Joseph Fortunak Christopher N. Boddy |
| Affiliation: | a Department of Chemistry, Syracuse University, Syracuse, NY 13244-4100, United States b ProcesScience Inc. Fayetteville, NY 13066, United States c Department of Pharmaceutical Science, School of Pharmacy, Howard University, 2300 4th Street, NW Washington, D.C. 20059, United States d Clinton Health Access Initiative, 383 Dorchester Ave, Suite 400, Boston, MA 02127, United States e Department of Chemistry, University of Ottawa, Ottawa, ON, Canada K1N 6N5 |
| Abstract: | 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. |
| Keywords: | Tenofovir Phosphoate ester hydrolysis TMSBr |
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