169331-42-4Relevant academic research and scientific papers
An Efficient Synthesis of a Hydroxyethylamine (HEA) Isostere and Its α-Aminophosphonate and Phosphoramidate Derivatives as Potential Anti-HIV Agents
Bhattacharya, Asish K.,Rana, Kalpeshkumar C.,Pannecouque, Christophe,DeClercq, Eric
, p. 1601 - 1611 (2012/10/29)
HIV protease is a promising drug target for AIDS therapy, and several potent HIV-1 protease inhibitors have been reported to date. Although existing inhibitors exhibit high selectivity, they have also been associated with severe side effects and the possi
Diastereoselective synthesis of N,N-dibenzyl-protected aminoalkyl hydroxyethylamines: Key building blocks for hydroxyethylamine-based BACE1 inhibitor
Wu, Jie,Gao, Shanyun,Liao, Guochao,Lin, Hansen,Nie, Aihua
experimental part, p. 2907 - 2916 (2012/07/28)
(Chemical Equation Presented) L-Amino acids were reduced with NaBH 4 followed by reacting with benzyl bromide to give N,N-dibenzyl-protected aminoalkyl ethanol 3, which in turn underwent a Swern oxidation, a Johnson-Corey-Chaykovsky reaction, and a nucleophilic reaction to afford N,N-dibenzyl-protected aminoalkyl hydroxyethylamine 6 with a diastereomer ratio 2.5-2.9:1 of (2R, 3S)-6:(2S, 3S)-6. Copyright Taylor & Francis Group, LLC.
Self-emulsifying drug delivery system
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Page 7-8, (2010/02/05)
Oral pharmaceutical formulation which improves the bioavailability of pharmaceuticals which are substantially water and oil insoluble is disclosed. In addition to the pharmaceutical, the formulation includes an emulsifier, an oil and an solubilizer. Alter
Preparation of aminoepoxides from aminoaldehydes and an in situ formed halomethyl organometallic reagent
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, (2008/06/13)
In a method of preparing an aminoepoxide wherein a protected aminoaldehyde is reacted with a halomethyl organometallic reagent in an appropriate solvent at a temperature above -80 DEG C., wherein said halomethyl organometallic reagent is formed by reaction between an organometallic reagent and a dihalomethane, the improvement comprising flowing said protected aminoaldehyde into a mixing zone maintained at a temperature below 0 DEG C., also flowing said halomethyl organometallic reagent in said mixing zone for contacting in said mixing zone with said protected aminoaldehyde and also withdrawing from said mixing zone reaction products of said protected aminoaldehyde and said halomethyl organometallic reagent.
Bis-amino acid hydroxyethylamino sulfonamide retroviral protease inhibitors
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Page column 36, (2008/06/13)
Selected bis-amino acid hydroxyethylamino sulfonamide compounds are effective as retroviral protease inhibitors, and in particular as inhibitors of HIV protease. The present invention relates to such retroviral protease inhibitors and, more particularly, relates to selected novel compounds, composition and method for inhibiting retroviral proteases, such as human immunodeficiency virus (HIV) protease, prophylactically preventing retroviral infection or the spread of a retrovirus, and treatment of a retroviral infection.
Epoxide formation by continuous in-situ synthesis process
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, (2008/06/13)
In a method of preparing an aminoepoxide wherein a protected aminoaldehyde is reacted with a halomethyl organometallic reagent in an appropriate solvent at a temperature above -80 DEG C., wherein said halomethyl organometallic reagent is formed by reaction between an organometallic reagent and a dihalomethane, the improvement comprising flowing said protected aminoaldehyde into a mixing zone maintained at a temperature below 0 DEG C., also flowing said halomethyl organometallic reagent in said mixing zone for contacting in said mixing zone with said protected aminoaldehyde and also withdrawing from said mixing zone reaction products of said protected aminoaldehyde and said halomethyl organometallic reagent.
re- and si-face-selective nitroaldol reactions catalyzed by a rigid chiral quaternary ammonium salt: A highly stereoselective synthesis of the HIV protease inhibitor amprenavir (Vertex 478)
Corey,Zhang, Fu-Yao
, p. 1931 - 1934 (2007/10/03)
Either amprenavir (1) or its C(2) diastereomer can be synthesized in a simple way by the use of a nitroaldol reaction carried out in the presence of one or the other of the two ammonium ions 2. The 1,3-diamino-2-hydroxypropyl structural element of 1 is also found in many other peptidomimetics and HIV protease inhibitors. Described here is a new strategy for possible application to direct and stereocontrolled synthesis of such compounds.
Preparation of aminoalkyl chlorohydrin hydrochlorides: Key building blocks for hydroxyethylamine-based HIV protease inhibitors
Beaulieu, Pierre L.,Wernic, Dominik
, p. 3635 - 3645 (2007/10/03)
Enantiomerically pure N,N-dibenzyl-α-amino aldehydes reacted with (chloromethyl)lithium, generated in situ from bromochloromethane and lithium metal, to give predominantly erythro aminoalkyl epoxides. Treatment of the crude epoxides with aqueous hydrochloric acid gave crystalline (2S,3S)-N,N-dibenzylamino chlorohydrin hydrochlorides in 32-56% overall yield and high isomeric purity. These compounds are versatile synthetic intermediates for the preparation of hydroxyethylamine-based HIV protease inhibitors, either directly as such, or via conversion to the corresponding N-Boc(2S,3S)-aminoalkyl epoxides. The processes described do not make use of hazardous reagents or intermediates, do not require chromatographic purifications, and are thus amenable to the preparation of large quantities of these versatile building blocks.
A Practical Synthesis of an HIV Protease Inhibitor Intermediate - Diastreoselective Epoxide Formation from Chiral α-Aminoaldehydes
Ng, John S.,Przybyla, Claire A.,Liu, Chin,Yen, Joe C.,Muellner, Frank W.,Weyker, Cara L.
, p. 6397 - 6410 (2007/10/02)
A practical and efficient synthesis of an HIV protease inhibitor intermediate has been developed based on the diastereoselective epoxide formation from a chiral α-aminoaldehyde and an in situ generated halomethyllithium reagent.
