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Ugi NMR Analysis
To synthesize a
) from Phenanthrene-9- carboxaldehyde, tert-butyl isocyanide, benzylamine, and crotonic acid in methanol using Ugi 4CR following
. This is a repeat of
.The target compound was ranked 155 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
[The experiment is repeated because Phenanthrene-9-carboxaldehyde which was used in the previous experiment was acquired as a liquid. The aldehyde used here was obtained from Sigma Aldrich as a solid- Mpt-100C]
To a one dram vial, charged with methanol (1mL) benzylamine, phenanthrene-9-carboxaldehyde, crotonic acid and tert-butyl isocyanide (0.5mmol each) was added in that order. After each addition, the resulting solution was vortexed for 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
Density information found on the Sigma-Aldrich website (www.sigmaaldrich.com)
5 min after mixing
all components (156A)
One day after mixing
all components (156B)
The experiment was repeated because Phenanthrene-9-carboxaldhyde which was used in the previous experiment was obtained as a liquid, the
of the liquid does not correspond to the
NMR of the compound
purchased from Sigma-Aldrich.
All results are recorded
Master Table and Workflow Tables
After one day a precipitate was obtained - analysis by NMR pending to confirm Ugi product.
17:22- Weighed out the Phenanthrene-9-carboxaldehyde.
17:30- Weighed out the crotonic acid.
17:39- Charged a vial with 1 ml of methanol.
17:42- Added the benzylamine to the vial and vortexed for 15 seconds. A clear solution was obtained.
17:44- Added the phenanthrene-9-carboxaldehyde and vortexted for 6 minutes before the solution was no longer cloudy. The solid went into the solution.
17:48- Added the crotonic acid and vortexed for one minute before the solution was not longer cloudy. A clear solution was obtained.
17:50- Added the tert-butyl isocyanide and vortexted for one minute. A clear solution was obtained.
17:55- A photo was taken after all of the components were mixed. The solution was left to sit for a day at room temperature.
17:45- The solution precipitated white crystals. A photo of the vial was taken.
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