122.JPG

Objective

To synthesize Ugi adducts following the EXPLAN005 . The compounds will contribute toward a library for enoyl reductase inhibitors.

Procedure

A Ugi reaction was carried out in a 1.5 ml Eppendorf tube. In the tube, methanol (500uL), methylamine (2.0M solution in methanol, 0.25mmol, 125uL), o-tolualdehyde (0.25mmol, 28.9uL), acetic acid (0.25mmol, 14.31uL), and p-toluenesulfonylmethyl isocyanide (0.25mmol, 48.8mg) were added, in that order.
After each addition the solution was vortexed for 15s and made sure a homogeneous solution was obtained. The Eppendorf tube was left at room temperature.

Results


Discussion

The solution remained clear after adding all of the compounds and allowing it to sit for 24 hours.

Conclusion

A Ugi product was not obtained.

Log

2007-08-15

11:00 Weighed Eppendorf tube (0.8228g) and labeled tube 122
11:30 Weighed out p-toluenesulforylmethyl isocyanide (48.8mg)
11:40 Filled tube with methanol (500uL), solution was clear
11:45 Added methylamine to solution (125uL)
11:50 Mechanically mixed on vortex for 15 seconds
11:55 Measured o-tolualdehyde (28.9uL) and added it to solution
12:00 Mechanically mixed on vortex for 15 seconds
12:05 Added acetic acid (14.31uL) to solution
12:10 Mechanically mixed on vortex for 15 seconds
12:15 Added p-toluenesulforylmethyl isocyanide (48.8mg) to solution, solution turned an orange color
12:20 Mechanically mixed on vortex for several minutes until everything was completely dissolved
12:30 Let solution sit undisturbed in the 1.5mL Eppendorf tube

2007-08-16

12:30 Observed no precipitate in tube

Tags

o-tolualdehyde InChI=1/C9H14/c1-6-7(2)9-4-3-8(6)5-9/h8-9H,3-5H2,1-2H3

include tags for all compounds in this experiment