Objective

To synthesize two Ugi products following the EXPLAN005 . The compound will contribute toward a library for Falcipain2 inhibitors.
These compounds were ranked 101 and 105 in the DEXP014-V1B

Procedure

As described in Explan005
Comp ID/ Lib Rank
Aldehyde
Amine
Carboxylic Acid
Isocyanide
Ppt Yes/No
142-1/101
phenanthrene-9-carboxaldehyde
(0.25mmol, 42.4uL)
Furfurylamine
(0.25mmol, 22.1uL)
Hippuric acid
(0.25mmol, 44.79mg)
Butyl isocyanide
(0.25mmol, 26.1uL)
Void
142-2/105
phenanthrene-9-carboxaldehyde(0.25mmol, 42.4uL)
Furfurylamine
(0.25mmol, 22.1uL)
Hippuric acid
(0.25mmol, 44.79mg)
t-butylisocyanide
(0.25mmol, 28.3uL)
Void

Results

All results are recorded in the Master Table of all Ugi synthesis attempts

Discussion

An error was made in the amount of hippuric acid added to the two samples. Due to the excess amount of hippuric acid added, the samples formed an insoluble, cloudy mixture. The results were void for this experiment

Conclusion

The results of this experiment are void as the measurements made for the hippuric acid were erroneous. Instead of 44.79 mg, 447.9 mg were added by accident to the mixture. This resulted in a precipitate that was due to insolubility rather than actual precipitate formed via reaction.

Log

2007-10-26

16:25: Weighed out hippuric acid (44.79 mg) on weighing paper
16:30: Added methanol (500uL) into the dram vials, followed by 30 seconds vortexing.
16:32: Added aldehyde into the dram vials, followed by 15 seconds vortexing.
16:34: Added amine into the dram vials, followed by 30 second vortexing.
16:36: Added acid into the dram vials followed by 15 second vortexing
16:40: Added isocyanide into dram vials followed by 15 second vortexing.
16:45: Let vials sit in fume hoods tonight


Tags

n-butylisocyanide InChI=1/C5H9N/c1-3-4-5-6-2/h3-5H2,1H3
phenanthrene-9-carboxaldehydeInChI=1/C15H10O/c16-10-12-9-11-5-1-2-6-13(11)15-8-4-3-7-14(12)15/h1-10H
t-butylisocyanideInChI=1/C5H9N/c1-5(2,3)6-4/h1-3H3
furfurylamine InChI=1/C5H7NO/c6-4-5-2-1-3-7-5/h1-3H,4,6H2
hippuric acid InChI=1/C9H9NO3/c11-8(12)6-10-9(13)7-4-2-1-3-5-7/h1-5H,6H2,(H,10,13)(H,11,12)/f/h10-11H