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Alicia's Masters Thesis
Open Web Drug Dev.
To Do List
Ugi NMR Analysis
To synthesize a Ugi adduct from
4-chlorobenzaldehyde, tosylmethyl isocyanide, 5-methylfurfurylamine, and salicylic acid in methanol using Ugi 4CR following
. The target compound was ranked 16 in the
. The purpose of this experiment is to synthesize an anti-malarial compound based on the inhibition of falcipain-2, as described in this
To a one dram vial, charged with methanol (1mL) 5-methylfurfurylamine, 4-chlorobenzaldehyde, salicylic acid and tosylmethyl isocyanide (0.5mmol each) was added in that order. After each addition, the resulting solution was vortexed for at least 15 seconds and confirmed that a homogeneous solution had been obtained. The vial was capped tight and left at room temperature for 1 day.
ID/ Lib Rank
0.5 mmol, 70.3 mg
0.5mmol, 96.6 mg
Density information found on the Sigma-Aldrich website (www.sigmaaldrich.com)
5 min after mixing
One day after mixing
All results are recorded
Master Table and Workflow Tables
After the vial set out at room temperature for a day and was sonicated, no Ugi product was formed.
16:55- Charged a vial with 1 mL of methanol.
17:01- Started to weigh out 4-chlorobenzaldehyde.
17:06- Started to weigh out salicylic acid.
17:10- Started to weigh out tosylmethyl isocyanide.
17:15- Added the 5-methylfurfurylamine to the vial and vortexed for 15 seconds. A clear solution was obtained.
17:17- Added the 4-chlorobenzaldehyde to the vial and vortexed for 15 seconds. A clear solution was obtained.
17:19- Added the salicylic acid to the vial and vortexed for 15 seconds. A clear solution was obtained.
17:22- Added the tosylmethyl isocyanide to the vial and vortexed for one minute. A clear solution was obtained.
17:25- A photo was taken after all of the components were mixed. The solution was left to sit for a day at room temperature.
17:33- Took picture of the vial. No precipitate has formed yet. The solution was very dark green
17:35- Put the vial into the sonicator for ten minutes.
17:45- Removed the vial from the sonicator. No precipitate has formed.
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