183.gif

Objective

To synthesize a Ugi Product following the EXPLAN005 with phenanthrene-9-carboxaldehyde, cyclohexylamine, mandelic acid and t-butyl isocyanide. The compound will contribute towards a library for Falcipain2 inhibitors.
This compounds was ranked 49 in the DEXP014-V1B file from D-EXP014 . The purpose of this experiment is to synthesize an anti-malarial compound based on the inhibition of falcipain-2, as described in this summary post.

Procedure

As described in Explan005
This reaction used Phenanthrene-9-carboxaldehyde, cyclohexylamine, t-butylisocyanide and Furoic acid.
Phenanthrene-9-Carboxaldehyde (solid from Sigma-Aldrich)
HNMR
ID/ Lib Rank
Solvent
Aldehyde
Amine
Carboxylic Acid
Isocyanide
Ppt Yes/No
183/49
Methanol
Phenanthrene-9-
carboxaldehyde
cyclohexylamine
Mandelic acid
t-butylisocyanide
Reagents
Insoluble
Quantity
1000uL
0.5mmol, 103.1mg
0.5mmol, 57.2uL
(density=0.867g/ml)
0.5mmol, 76.075 mg
0.5mmol, 56.5uL
(density=0.735g/ml)


Density information found on the Ugi Chemicals Page in Left Navigation Bar.

Results

Photos taken directly after all the components were charged and vortexed.
183A
Exp183A.JPG


Discussion



Conclusion

The starting materials are insoluble.

Log

2008-04-16

15:12- Charged a vial with 1000 ul of methanol.
15:14- Weighed out the Phenanthrene-9-carboxaldehyde.
15:18- Added the cyclohexylamine to the vial.
15:19- Vortexed vial 15 seconds.
15:22- Added the phenanthrene-9-carboxaldehyde.
15:23- Vortexed vial 2 min. No clear solution was obtained.
15:27- Added the mandelic acid.
15:30- Vortexed vial 3 min. No clear solution was obtained.
15:34- Added the t-butyl isocyanide.
15:36- Vortexed 5 min. No clear solution was obtained.
15:44- A photo was taken (183A).


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 InChIKey QECIGCMPORCORE-UHFFFAOYAE
tert-butyl isocyanideInChI=1/C5H9N/c1-5(2,3)6-4/h1-3H3 InChIKey FAGLEPBREOXSAC-UHFFFAOYAL
Mandelic acid InChI=1/C8H8O3/c9-7(8(10)11)6-4-2-1-3-5-6/h1-5,7,9H,(H,10,11)/t7-/m0/s1 InChIKey IWYDHOAUDWTVEP-UHFFFAOYAD
cyclohexylamineInChI=1/C6H13N/c7-6-4-2-1-3-5-6/h6H,1-5,7H2InChIKeyIFYLVUHLOOCYBG-UHFFFAOYAD