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Alicia's Masters Thesis
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To Do List
Ugi NMR Analysis
To synthesize a
from aniline, phenanthrene-9-carboxaldehyde, phenyl acetic acid and n-butyl isocyanide in methanol using Ugi 4CR following
. The target compound was ranked 20 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) and aniline, phenanthrene-9-carboxaldehyde, phenyl acetic acid and n-butyl 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
phenyl acetic acid
0.5 mmol, 103.12 mg
0.5mmol, 68.08 mg
0.5mmol, 52.28 ul
Density information found on the Sigma-Aldrich website (www.sigmaaldrich.com)
5 min after mixing
all components (164A)
All results are recorded
Master Table and Workflow Tables
This Ugi reaction failed to dissolve, possibly due to the apparent selective solubility of phenanthrene-9-carboxaldehyde as discussed
15:37- Charged a vial with 1 ml of methanol.
15:39- Started to weigh out the phenanthrene-9-carboxaldehyde
15:45- Started to weigh out the phenylacetic acid.
15:49- Added the aniline to the vial and vortexed for 15 seconds. A clear solution was obtained.
15:52- Added the phenanthrene-9-carboxaldehyde to the vial and vortexed for 6 minutes. No clear solution was obtained.
15:59- Added the phenylacetic acid and vortexed for 5 minutes. No clear solution was obtained.
16:08- Added the n-butylisocyanide and vortexed for 5 minutes. No clear solution was obtained.
16:15- Added another 0.5 ml of methanol to the vial and vortexed for one minute. There was no change in the vial and no clear solution.
16:17- Vortexed for 5 more minutes. No clear solution was obtained.
16:25- Took a photo of the vial. This experiment needs to be aborted, because the components did not all go into solution.
phenyl acetic acid
InChI=1/C3 4H32N2O2/c1-2-3-22-35-34(38)33(31-24-26-16-10-11-19-28(26)29 -20-12-13-21-30(29)31)36(27-17-8-5-9-18-27)32(37)23-25-14-6- 4-7-15-25/h4-21,24,33H,2-3,22-23H2,1H3,(H,35,38)
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