Objective

To synthesize two Ugi products following the EXPLAN005 . The compound will contribute toward a library for Falcipain2 inhibitors. This experiment is a re-do of Exp141.
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
141-1/101
phenanthrene-9-carboxaldehyde
(0.25mmol, 42.4uL)
Furfurylamine
(0.25mmol, 22.1uL)
Hippuric acid
(0.25mmol, 44.8mg)
Butyllisocyanide
(0.25mmol, 26.1uL)
No
141-2/105
phenanthrene-9-carboxaldehyde (0.25mmol, 42.4uL)
Furfurylamine
(0.25mmol, 22.1uL)
Hippuric acid
(0.25mmol, 44.8mg)
t-butylisocyanide
(0.25mmol, 28.3uL)
No


Results

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

Picture of solutions soon after the addition of all components (142A)
picture1rev.JPG
why did you delete the request to put pic 142B? - the log says it exists and you need it to support your conclusion

Discussion

This time, the solubility issue was resolved. Unfortunately, no precipitate formation occurred. An important lesson, however, did come from these experiments. It elucidates how important it is to be careful during the measuring periods of sample preparation. Full attention is required when weighing out the samples because even if one compound is improperly weighed, it can lead to erroneous results. Fortunately, the insolubility in this case allowed us to catch the mistake. However, in the future, the error may not be as easy to spot.

Conclusion

There was no precipitate (you need to provide evidence for this) shown in any of the vials. It confirms that Experiment 141 showed precipitate due to the insolubility of excess hippuric acid and not the actual formation of precipitate via reaction.

Log

2007-10-31

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 seconds vortexing.
16:36: Added acid into the dram vials followed by 15 seconds vortexing
16:40: Added isocyanide into dram vials followed by 15 seconds vortexing
16:42: Picture of dram vials was taken 142A
16:44: Vials were kept in hood overnight

2007-11-01

13:00: Vials were looked at and determined to have no precipitate
13:02: Picture of dram vials was taken 142B

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