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UC on ChemSpider
Alicia's Masters Thesis
Open Web Drug Dev.
To Do List
Ugi NMR Analysis
To synthesize one Ugi product following the
. The compound will contribute towards a library for falcipain-2 inhibitors. This compounds was ranked 12 in the
As described in
One Ugi reaction was carried out in a vial labeled Exp153-1.To one dram vial was added methanol (500 ul), phenanthrene-9-carboxaldehyde (0.5mmol, 503.1mg), methylamine(in 2M methanolic solution, yielding 250 ul for 0.5mmol), 1-pyrenebutyric acid (0.5mmol, 144.1mg), another 500 ul of methanol, and t-butyl isocyanide (0.5mmol, 56.5ul), in that order. After each addition, the solution was vortexed for 15 seconds. The vial was also sonicated for one hour immediately after the addition of all components.The formation or absence of precipitate was noted. The dram vials were left at room temperature.
Phenanthrene-9-carboxaldehyde (0.5 mmol, 103.1 mg)
Methylamine (250uL,0.5mmol, 2M methanolic solution)
1-pyrenebutyric acid (0.5mmol, 144.1 mg)
t-butyl isocyanide (0.5mmol, 56.6ul)
reactant insolubility problem
All results are recorded in the
Master Table of all Ugi Synthesis Attempts
Photo of 153-1-A taken at 16:14 immediately after adding all components (before sonification):
Speculate about what might be causing lack of solubility - is your experience consistent with what others in our group have observed?
The lack of solubility may arise from the fact that the amount of methanol in the normal procedure was insufficient to dissolve the compounds. Also, the compound was noted as insoluble upon the addition of 1-pyrenebutyric acid. Various factors may exist that could have caused this insolubility, including contamination of the aldehyde, amine, or acid. The acid utilized, 1-pyrenebutyric acid, was also used before Exp 153, in
, and the sample went into solution immediately following the the appropriate vortexing. At this point, an alternate cause of this insolubility in Exp 153 may also stem from the components not being able to solubilize with each other if contamination is negative.
But which compound specifically are you saying is insoluble? And if you are saying that a component is insoluble at this concentration, is that what all the other experiments report?
15:30 Weighed out phenanthrene 9-carboxaldehyde and 1-pyrenebutyric acid weighing paper
15:40: Added methanol (
) into the dram vials, followed by 15 seconds vortexing.
15:52: Added aldehyde into the dram vials, followed by 15 seconds vortexing.
15:57: Added amine into the dram vials, followed by 15 seconds vortexing.
16:00: Added acid into the dram vials followed by 15 seconds vortexing
16:05: Noticed poor solubility and added another 500 ul of methanol to vial, followed by 15 seconds of vortexing
16:10: Added isocyanide into dram vials followed by 15 seconds vortexing
16:14: Took picture of vial (153-1-A) before placing into sonicator
16:15: Placed vial in sonicater for one hour.
17:15: After one hour of sonification, solution still remained inhomogenous.
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