Journal article
Optimization of the Ugi Reaction Using Parallel Synthesis and Automated Liquid Handling
Journal of Visualized Experiments, (21)
2008
PMID: 19066532
Abstract
The optimization of a Ugi reaction involving the mixing of furfurylamine, benzaldehyde, boc-glycine and t-butylisocyanide is described. Triplicate runs of 48 parallel experiments are reported, varying concentration, solvent and the excess of some of the reagents. The isolation of the product was achieved by a simple filtration and wash procedure. The highest yield obtained was 66% from 0.4 M methanol with 1.2 eq. of imine. This is significantly above the 49% yield obtained from the initial reaction under equimolar concentration at 0.4 M in methanol. Methanol solutions with reagent concentrations of 0.4M or 0.2M gave superior yields while all solvent systems at 0.07M performed poorly. At 0.2M, methanol and ethanol/methanol (60/40) mixtures were statistically equally good while THF/methanol (60/40) was poor and acetonitrile/methanol (60/40) was intermediate. Good reproducibility of the precipitate yields was obtained in these replicate experiments, allowing for subtle interaction effects to be positively identified.
Metrics
8 Record Views
6 citations in Scopus
Details
- Title
- Optimization of the Ugi Reaction Using Parallel Synthesis and Automated Liquid Handling
- Creators
- Jean-Claude Bradley - Department of Chemistry, Drexel UniversityKhalid Baig Mirza - Department of Chemistry, Drexel UniversityTom Osborne - Mettler-ToledoAntony Wiliams - ChemspiderKevin Owens - Department of Chemistry, Drexel University
- Publication Details
- Journal of Visualized Experiments, (21)
- Publisher
- MyJove Corporation
- Resource Type
- Journal article
- Language
- English
- Academic Unit
- Chemistry
- Scopus ID
- 2-s2.0-80055106014
- Other Identifier
- 991014877672904721