exp163.gif

Objective

To synthesize a Ugi product from phenanthrene-9-carboxaldehyde, furfurylamine, Mandelic acid, and t-butylisocyanide following the EXPLAN005 . The compound will contribute towards a library for Falcipain2 inhibitors.
This compunds was ranked 14 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

ID/ Lib Rank
Solvent
Aldehyde
Amine
Carboxylic Acid
Isocyanide
Ppt Yes/No
157/14
Methanol
Phenanthrene-9-
carboxaldehyde
furfurylamine
hydroxy(phenyl)acetic acid
[Mandelic acid] racemic
tert-butylisocyanide
no
Quantity
1000uL
0.5mmol, 103.1mg
.5mmol, 44.18 ul
0.5mmol, 76.075 mg
0.5mmol, 56.5uL
(density=0.735g/ml)


Density information found on the Ugi ChemicalsUgi Chemicals.

Results


5 min after mixing
all components (Exp163A)

One day after mixing
all components (Exp163A1)

exp163A.jpg
Exp163A1.jpg
Two days after mixing
all components (Exp163A2)

Exp163A2.jpg

All results are recorded Master Table and Workflow Tables .

Discussion

A clear yellow solution was obtained after all the reactants were added and vortexed as well as sonicated, what is interesting is that once the isocyanide was added to the solution it seemed to help with the overall solubility of the solution.

Conclusion

No precipitate was observed after 24 hours.

Log

2008-01-24

15:22- Methanol added to one dram vial.
15:24- Furfurylamine was added to the vial and solution was vortexed for 20 seconds.
15:30-Weighed out Phenanthrene-9-carboxaldehyde.
15:32- Added Phenanthrene-9-carboxaldehyde to solution and vortexed for 20 seconds, a homogenous solution was not formed thus the solution was sonicated for 5 minutes, and still no homogeneous solution was formed.
15:38- Weighed out Mandelic acid.
15:40- Added Mandelic acid and vortexed for 20 seconds, no homogeneous solution was formed thus the solution was sonicated for 5 minutes.
15:46- Isocyanide was added to the solution and the vial was vortexed for 20 seconds and sonicated for 10 minutes.
15:56- A homogenous mixture was obtained.
16:00- A picture 163A of the vial was taken.
2008-01-25
15:16- Picture 163A1 was taken 24hrs after reaction.
2008-01-26
14:02- Solution was vortexed for 15 seconds.
14:03 Picture 163A2 was taken.
2008-03-13 12:52 Obtained HNMR of Mandelic Acid

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
Furfurylamine InChI=1/C5H7NO/c6-4-5-2-1-3-7-5/h1-3H,4,6H2InChIKey DDRPCXLAQZKBJP-UHFFFAOYAX
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
UgiProduct InChI=1/C33H32N2O4/c1-33(2,3)34-31(37)29(28-20-23-14-7-8-16-25(23)26-17-9-10-18-27(26)28)35(21-24-15-11-19-39-24)32(38)30(36)22-12-5-4-6-13-22/h4-20,29-30,36H,21H2,1-3H3,(H,34,37) InChIKey KWDYVEIXHGZXHC-UHFFFAOYAW