exp163.gif

Objective

To synthesize a Ugi products 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 .

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] (is this one enantiomer or racemic?)
dl-mandelic acid
tert-butylisocyanide

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 Sigma-Aldrich website (www.sigmaaldrich.com)

Results



All results are recorded Master Table and Workflow Tables .


Conclusion

Experiment aborted because a clear solution was never obtained immediately after mixing all reagents or the addition of extra solvent. However no pics were taken to document this so the experiment will have to be repeated.

Log

2008-01-24

15:22- Methanol added to one dram vial.
15:23- Furfurylamine was added to the vial and solution was vortexed for 20 seconds.
15:24-Weighed out Phenanthrene-9-carboxaldehyde.
15:26- 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.
15:32- Weighed out Mandelic acid.
15:34- Added Mandelic acid and vortexed for 20 seconds, no homogeneous solution was formed thus the solution was sonicated for 5 minutes.
15:41- Isocyanide was added to the solution and the vial was vortexed for 20 seconds and sonicated for 5 minutes.
15:47- No homogenous mixture was obtained.
15:50- 1000ul of methanol was added to try and help the mixture go into solution, and vortexed for 5 minutes.
15:55- No solution was obtained.

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