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Alicia's Masters Thesis
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Ugi NMR Analysis
To synthesize Ugi adducts following the
. The compounds will contribute toward a library for enoyl reductase inhibitors.
A Ugi reaction was carried out in a 1.5 ml Eppendorf tube. In the tube, methanol (500uL), methylamine (2.0M solution in methanol, 0.25mmol, 125uL), o-tolualdehyde (0.25mmol, 28.9uL), acetic acid (0.25mmol, 14.31uL), and
-toluenesulfonylmethyl isocyanide (0.25mmol, 48.8mg) were added, in that order.
After each addition the solution was vortexed for 15s and made sure a homogeneous solution was obtained. The Eppendorf tube was left at room temperature.
The solution remained clear after adding all of the compounds and allowing it to sit for 24 hours.
A Ugi product was not obtained.
11:00 Weighed Eppendorf tube (0.8228g) and labeled tube 122
11:30 Weighed out p-toluenesulforylmethyl isocyanide (48.8mg)
11:40 Filled tube with methanol (500uL), solution was clear
11:45 Added methylamine to solution (125uL)
11:50 Mechanically mixed on vortex for 15 seconds
11:55 Measured o-tolualdehyde (28.9uL) and added it to solution
12:00 Mechanically mixed on vortex for 15 seconds
12:05 Added acetic acid (14.31uL) to solution
12:10 Mechanically mixed on vortex for 15 seconds
12:15 Added p-toluenesulforylmethyl isocyanide (48.8mg) to solution, solution turned an orange color
12:20 Mechanically mixed on vortex for several minutes until everything was completely dissolved
12:30 Let solution sit undisturbed in the 1.5mL Eppendorf tube
12:30 Observed no precipitate in tube
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