1003888-24-1Relevant articles and documents
An efficient and practical synthesis of the HIV protease inhibitor atazanavir via a highly diastereoselective reduction approach
Fan, Xing,Song, Yan-Li,Long, Ya-Qiu
, p. 69 - 75 (2008)
An efficient and practical synthesis of the HIV-1 protease inhibitor Atazanavir was developed by employing the diastereoselective reduction of ketomethylene aza-dipeptide isostere 10 as the key and final step. The high diastereoselectivity of the amino ketone reduction by lithium tri-iert-butoxyaluminum hydride in diethyl ether to afford the desired svn-1,2-amino alcohol structure was achieved by Felkin- Anh control as a result of the bulky and chiral N-(methoxycarbonyl)-L-tert-leucinyl moiety as the nitrogen protecting group. The coupling of the two key intermediates, N-(methoxycarbonyl)-L-tert-leucine acylated benzyl hydrazine 7 and chloromethyl ketone 9, via an SN2 reaction furnished the amino ketone 10 in high yield under our optimized conditions. Our new methodology features the late introduction of the S-hydroxyl group and the early acylation of benzyl hydrazine and chloromethyl ketone with N-(methoxycarbonyl)-L-tert-leucine, respectively, which confers high efficiency and easy purification.
PROCESS FOR SYNTHESIZING ATAZANAVIR
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Page/Page column 40-41, (2009/12/05)
This invention relates to a process for synthesizing Atazanavir, Formula (I), including novel intermediates and novel steps to various intermediates along the synthetic pathway.
ANTIVIRAL PROTEASE INHIBITORS
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Page/Page column 453-454; 510, (2008/06/13)
The invention is related to compounds of Formula I or a pharmaceutically acceptable salt, solvate, ester, and /or phosphonate thereof, compositions containing such compounds, and therapeutic methods that include the administration of such compounds.