223410-63-7Relevant academic research and scientific papers
Quaternary chiral center via diastereoselective enolate amination enables the synthesis of an anti-inflammatory agent
Magnus, Nicholas A.,Campagna, Silvio,Confalone, Pat N.,Savage, Scott,Meloni, David J.,Waltermire, Robert E.,Wethman, Robert G.,Yates, Mathew
experimental part, p. 159 - 167 (2010/04/29)
The D-leucine amino acid residue necessary for the synthesis of BMS-561392,1, was employed as a chiral directing group for a diastereoselective enolate animation to establish the quaternary chiral center. Enhanced diastereomeric ratios were observed while conducting the enolate amination with 1-chloro-1-nitrosocyclo- pentane 6 in the presence of LiCl. Analogies are drawn between known tertiary amide amino alcohol chiral auxiliaries which have been used to effect diastereoselective enolate alkylations and aminations. Once the stereochemical features of 1 were established, an efficient reaction sequence was devised to complete its synthesis. During the course of this research, accelerated reaction calorimetry (ARC) data substantiated that the aminating agent 1-chloro-1- nitrosocyclopentane 6 was not safe to use as a neat compound. Consequently, a preparation and use of 6 as a stock solution in methyl tert-butyl ether (MTBE) was developed that rendered it safe for use.
Lactam derivatives as inhibitors of matrix metalloproteinases and/or TNF-alpha converting enzyme
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Page/Page column 20, (2010/02/10)
The present invention provides compounds of Formula (I): or a stereoisomer or pharmaceutically acceptable salt form thereof, wherein the variables A, B, R1, R2, U, X, Y, Z, Ua, Xa, Ya, and Za /s
ASYMETRIC SYNTHESIS OF AMINO-PYRROLIDINONES
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Page 45-46, (2010/02/04)
A novel process for the asymmetric synthesis of an amino-pyrrolidinone of the type shown below from appropriate pyrrolidinones is described. [Insert Chemical Formula] These compounds are useful as intermediates for MMP and TACE inhibitors.
