1089403-57-5Relevant academic research and scientific papers
Preparation of a HMG-CoA reductase inhibitor via an optimized imidazole-forming condensation reaction
Bowles, Daniel M.,Bolton, Gary L.,Boyles, David C.,Curran, Timothy T.,Hutchings, Richard H.,Larsen, Scott D.,Miller, Jonathan M.,Park, William K. C.,Ritsema, Kurtis G.,Schineman, David C.,Tamm, Markus
, p. 1183 - 1187 (2008)
Development work toward an enabling synthesis of preparative scale batches of an imidazole-based HMG-CoA reductase inhibitor is described. The desired target was synthesized in 16% yield over 7 steps, highlighted by an imidazole-forming condensation reaction in which the yield was improved from 20% to >70% via modification of the solvent, acid, and amine equivalents. The step 2 acylation was improved, and a problematic benzyl ester in step 4 was converted into the corresponding benzyl amide to decrease trans-amidation during the step 5 imidazole formation. A highly effective salt formation and crystallization protocol was also developed.
Synthesis of benzoate-functionalized phosphanes as novel building blocks for the traceless staudinger ligation
Mamat, Constantin,Flemming, Anke,Koeckerling, Martin,Steinbach, Joerg,Wuest, Frank R.
experimental part, p. 3311 - 3321 (2010/03/03)
A new synthetic pathway for the preparation of benzoate-functionalized phosphanes for microwave-mediated traceless Staudinger ligations is described. Novel phosphane derivatives based on 4-substituted iodophenyl benzoates were prepared via palladium(II)-catalyzed P-C cross-coupling reaction strategy in high yields. The application of microwave conditions for the ligation reactions reduced the reaction time considerably. An approach to fast and facile labeling strategies using this ligation was established.
