exp176cs.gif
Reaction Scheme

Objective

To synthesize a Ugi Product following the EXPLAN005 . The compound will contribute towards a library for Falcipain2 inhibitors.
This compounds was ranked 29 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 is a repeat of Experiment 176 to make sure that I also got a positive result, because every other experiment I have attempted failed to dissolve/ form a precipitate.

Procedure

As described in Explan005
This reaction used Phenanthrene-9-carboxaldehyde, furfurylamine, n-butyl isocyanide and phenylacetic acid.
Phenanthrene-9-Carboxaldehyde (solid from Sigma-Aldrich)
HNMR
ID/ Lib Rank
Solvent
Aldehyde
Amine
Carboxylic Acid
Isocyanide
Ppt Yes/No
178/29
Methanol
Phenanthrene-9-
carboxaldehyde
furfurylamine
Phenylacetic acid
n-butylisocyanide
Yes
Quantity
1000uL
0.5mmol, 103.1mg
0.5mmol, 44.2uL
(density=1.099g/ml)
0.5mmol, 68.1mg
0.5mmol, 52.3uL
(density=0.795g/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.
rank_29.JPG
178A
rank_29_day_2.JPG
178B


All results are recorded Master Table and Workflow Tables .

Discussion

This experiment demonstrated that I could successfully produce a precipitate from a control Ugi reaction that is known to have a positive result. This also supports my theory that the solubility of phenanthrene-9-carboxaldehyde is dependent on the amine. Furfurylamine has an oxygen in the ring, which increases its reactivity and allows it to participate in hydrogen bonding, thus making it soluble in methanol.

Conclusion

Experiment was successful with the formation of a precipitate. Experiment proved that I am completing experiments correctly. A further discussion of the apparent amine selective solubility of phenanthrene-9-carboxaldehyde is presented here.

Log

2008-02-28

15:44- Weighed out the Phenanthrene-9-carboxaldehyde.
15:50- Weighed out the phenylacetic acid.
15:55- Charged a vial with 1000 ul of methanol.
16:15- Added the furfurylamine to the vial.
16:16 Vortexed vial 1 min
16:17- Added the phenanthrene-9-carboxaldehyde.
1618-Vortexed vial 1 min
16:19- Added the phenylacetic acid.
16:20-Vortexed vial 1 min
16:21- Added the n-butyl isocyanide.
16:22-Vortexed 13min.
16:35-A clear solution was obtained
16:35- A photo was taken (178A) after the dissolution of all the reagents

2008-02-28

13:05 A photo was taken showing the formation of a precipitate (178B)

Tags

furfurylamine InChI=1/C5H7NO/c6-4-5-2-1-3-7-5/h1-3H,4,6H2 InChIKey: DDRPCXLAQZKBJP-UHFFFAOYAX
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 QECIGCMPORCORE-UHFFFAOYAE
phenylacetic acid InChI=1/C8H8O2/c1-7(9)10-8-5-3-2-4-6-8/h2-6H,1H3 WLJVXDMOQOGPHL-UHFFFAOYAR
n-butyl isocyanide InChI=1/C5H9N/c1-3-4-5-6-2/h3-5H2,1H3 InChIKey: FSBLVBBRXSCOKU-UHFFFAOYAR
Ugi Product InChI=1/C3 ​3H32N2O3/c​1-2-3-19-3​4-33(37)32​(30-22-25-​14-7-8-16-​27(25)28-1​ 7-9-10-18-​29(28)30)3​5(23-26-15​-11-20-38-​26)31(36)2​1-24-12-5-​ 4-6-13-24/​h4-18,20,2​2,32H,2-3,​19,21,23H2​,1H3,(H,34​,37) InChIKey: RGGYLRDGJAJICY-UHFFFAOYAH