Objective

To synthesize a Ugi product (link) following the EXPLAN005 . The compound will contribute towards a library for Falcipain2 inhibitors.
This compunds was ranked 11 in the DEXP014-V1B file from D-EXP014 . link to blog post summary

Procedure

As described in Explan005

ID/ Lib Rank
Solvent
Aldehyde
Amine
Carboxylic Acid
Isocyanide
Ppt Yes/No
157/11
Methanol
Phenanthrene-9-
carboxaldehyde
cyclohexylamine
Phenylacetic acid
tert-butylisocyanide
Aborted
Quantity
1000uL
0.5mmol, 103.1mg
0.5mmol, 57.2uL
(density=0.867g/ml)
0.5mmol, 68.1mg
0.5mmol, 56.5uL
(density=0.735g/ml)


Density information found on the Sigma-Aldrich website (www.sigmaaldrich.com)

Results

Photos taken directly after all the components were charged and vortexed.
Shannon_157-11_002.jpg
Exp157-11 no flash

Exp157-11 day 1
157A (8 minutes)

Shannon_157-11_day_2_002.jpg
Exp157/11 day 2

Exp157/11 day 2
157B (24 hours)

Discussion

The experiment was repeated because Phenanthrene-9-carboxaldhyde which was used in the previous experiment was obtained as a liquid, the HNMR 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 .


Conclusion

Experiment aborted because a clear solution was not obtained immediately after mixing all reagents.

Log

2008-01-15

16:07- Weighed out the Phenanthrene-9-carboxaldehyde.
16:13- Weighed out the phenylacetic acid.
16:19- Charged a vial with 500 ul of methanol.
16:22- Added the cyclohexylamine to the vial.
16:25- Added the phenanthrene-9-carboxaldehyde.
16:30- Added the phenylacetic acid.
16:32- Added the tert-butyl isocyanide and vortexted for one minute. First a chunky opaque solution was observed, and the vial was vortexed further until a homogeneous solution was obtained.
16:40- A photo was taken (157A) after all of the components were mixed. The solution was left to sit for a day at room temperature.

2008-01-16
17:45- The solution precipitated white extremely fine crystals. It was placed in ultrasonicator for 5 minutes. A photo of the vial was
taken. (157B).

Tags

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
tert-butylisocyanideInChI=1/C5H9N/c1-5(2,3)6-4/h1-3H3
cyclohexylamineInChI=1/C6H13N/c7-6-4-2-1-3-5-6/h6H,1-5,7H2
phenylacetic acid InChI=1/C8H8O2/c1-7(9)10-8-5-3-2-4-6-8/h2-6H,1H3
also include the Ugi product and InChIKeys for all