Objective

To synthesize 3 Ugi products following the EXPLAN005 . The compound will contribute towards a library for Falcipain2 inhibitors.
These compunds were ranked 11-13 in the DEXP014-V1B file from D-EXP014.

Procedure

As described in Explan005
Variation to the given procedure: instead of 0.5 mmol of each compound, 0.25 mmol were used in a solution of 250 ul of methanol.

Comp ID/ Lib Rank
Aldehyde
Amine
Carboxylic Acid
Isocyanide
Ppt Yes/No
138-4/ 14
Phenanthrene-9-carboxaldehyde
furfurylamine
hydroxy(phenyl)acetic acid [Mandelic Acid]
t-butylisocyanide
aborted
138-5/ 15
Phenanthrene-9-carboxaldehyde
Cyclohexylamine
3,4-dihydroxyphenyl acetic acid
t-butylisocyanide
aborted
138-8/ 18
Phenanthrene-9-carboxaldehyde
Benzylamine
4-chlorophenyl acetic acid
n-butylisocyanide
aborted

Results

None of the attempted Ugi products provided a precipitate, due to the fact that most of those attempted used a phenanthrene-9-carboxaldehyde, which the bottle in stock was found to be problematic, explained in the conclusion. Photographs are not provided because the batteries in the digital camera were dead and I was unable to locate replacements while I was in the lab.

Discussion

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

Conclusion

No results - experiment aborted due to a contaminated bottle of phenanthrene-9-carboxaldehyde which was found to be providing false negative results. All compounds will be re-attempted in new experiments.

Log

2007-11-1

1:30 Charge acids for vials 4, 5 and 8 1:45 Charge aldehydes for vials 4, 5 and 8 2:00 Charge amines for vials 4, 5 and 8 2:15 Charge isocyanides for vials 4, 5 and 8 2:30 Vortex all vials

2007-11-2

3:00 Vials were looked at and determined to have no precipitates