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. This experiment was conducted to obtain more data on the solubility of these starting materials in various solvents.

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

This experiment is Ranked 49. It is a repeat of Exp 183 in three different solvents: ethanol, acetonitrile, and dichloromethane.
Exp184-1 is in ethanol, Exp184-2 is in acetonitrile, and Exp184-3 is in dichloromethane.

ID/ Lib Rank
Solvent
Aldehyde
Amine
Carboxylic Acid
Isocyanide
Ppt Yes/No
184-1/49
ethanol
Phenanthrene-9-
carboxaldehyde
cyclohexylamine
Mandelic acid
t-butylisocyanide
Reagents Insoluble
184-2/49
acetonitrile
Phenanthrene-9-
carboxaldehyde
cyclohexylamine
Mandelic acid
t-butylisocyanide
Reagents Insoluble
184-3/49
dichloromethane
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.
184-1 A
184-2 A
184-3 A
Exp184-1.JPG
Exp184-2.JPG
Exp184-3.JPG


Discussion

Some of the materials were soluble - discuss this. Also your acid might not have been the best choice as a trial run -why?

Conclusion

The starting materials are insoluble in each solvent.

Log

2008-05-01

15:33- Charged vial 184-1 with 1000 ul of ethanol.
15:35- Charged vial 184-2 with 1000 ul of acetonitrile.
15:39- Charged vial 184-3 with 1000 ul of dichloromethane.
15:44- Weighed out the Phenanthrene-9-carboxaldehyde and mandelic acid for each of the three samples.
15:55- Added the cyclohexylamine to the vials.
15:59- Vortexed each vial 15 seconds each. Each sample was clear.
16:02- Added the phenanthrene-9-carboxaldehyde to each vial.
16:04- Vortexed vials for 3 minutes each. No clear solutions were obtained for Exp184-1 and Exp184-2. Vial Exp184-3 was clear.
16:14- Added the mandelic acid to each vial.
16:17- Vortexed vial 3 min. No clear solution was obtained.
16:27- Added the t-butyl isocyanide to each vial.
16:30- Vortexed 2 minutes each. No clear solutions were obtained.
16:38- Photos were taken of the vials 184-1 A, 184-2 A, and 184-3 A.


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