1104077-76-0Relevant academic research and scientific papers
In situ FTIR study and scale-up of an enolization - Azidation sequence
Connolly, Terrence J.,Hansen, Eric C.,MacEwan, Michael F.
, p. 466 - 469 (2010)
A key step in the synthesis of an optically active aminoalcoholcontaining active pharmaceutical ingredient (API) involved the diastereoselective introduction of an azido functional group on a functionalized chiral oxazolidinone. This was accomplished via a low-temperature enolization, followed by a quench with triisopropylbenzenesulfonyl azide. To enable scale-up of this process, the enolization temperature had to be increased from the original -65 °C to approximately -40 °C. In situ FTIR was used to study the enolization and quench stages of the reaction. The half-life of the enolate at -45 °C was estimated to be 12 h on the basis of in situ FTIR profiling. Examination of the in situ FTIR data also provided evidence that the reaction between the enolate and triisopropylbenzenesulfonyl azide was instantaneous and demonstrated that accumulation of triisopropylbenzenesulfonyl azide did not occur. A combination of in situ FTIR experiments and traditional parameter ranging experiments resulted in a process that was successfully run at -40 °C without an appreciable erosion of facial selectivity or yield.
PROCESS FOR THE PREPARATION OF TRIFLUOROALKYL-PHENYL AND HETEROCYCLIC SULFONAMIDES
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Page/Page column 14, (2009/02/11)
A novel trifluoroacetylating agent, i.e., N-trifluoroacetylmorpholine, is described. This reagent is useful in the preparation of phenyl and heterocyclic sulfonamide compounds. Methods are therefore described for preparing sulfonamide compounds of the fol
PROCESSES AND INTERMEDIATES FOR THE PREPARATION OF HETEROCYCLIC SULFONAMIDE COMPOUNDS
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Page/Page column 23, (2009/02/11)
Methods for preparing compound of formula (I) are described, wherein R1-R3 are defined herein, as are methods for preparing the intermediates formed therein. Also described are methods for enantioselectively preparing a chiral compou
Practical enantioselective synthesis of a 3-aryl-3-trifluoromethyl-2- aminopropanol derivative
Alimardanov, Asaf,Nikitenko, Antonia,Connolly, Terrence J.,Feigelson, Gregg,Chan, Anita W.,Ding, Zhixian,Ghosh, Mousumi,Shi, Xinxu,Ren, Jianxin,Hansen, Eric,Farr, Roger,MacEwan, Michael,Tadayon, Sam,Springer, Dane M.,Kreft, Anthony F.,Ho, Douglas M.,Potoski, John R.
body text, p. 1161 - 1168 (2010/04/22)
Development of a large-scale enantioselective synthesis of a lead compound containing a 3-aryl-3-trifluoromethyl-2-aminopropanol core is described. A single isomer of 3,3-disubstituted acrylic acid derivative was prepared via Perkin condensation or Horner
