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), furfuylamine (0.25mmol, 22.1uL), o-vanillin (0.25mmol, 38mg), Boc-Tryptophan (0.25mmol, 76.1mg), and n-butyl isocyanide (0.25mmol, 26.1uL) 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

There was no precipitate observed in the solution after sitting overnight.

Conclusion

A Ugi product was not obtained.

Log

2007-08-15

13:30 Weighed Eppendorf tube (0.8195g) and labeled
13:35 Weighed out o-vanillin (38mg)
13:45 Weighed out Boc-Tryptophan (76.1mg)
13:50 Filled tube with methanol (500uL), solution was clear
13:55 Added furfurylamine (22.1uL) to tube
13:58 Mechanically mixed on vortex for 15 seconds
14:00 Added o-vanillin (38mg) to tube, solution turned into a bright yellow color
14:02 Mechanically mixed on vortex for 15 seconds
14:05 Added Boc-Tryptophan (76.1mg) to solution
14:07 Mechanically mixed on vortex for 15 seconds
14:15 Added n-butyl isocyanide (26.1uL) to solution
14:17 Mechanically mixed on vortex for 15s, everything was completely dissolved
14:20 Let solution sit undisturbed in the 1.5mL Eppendorf tube

2007-08-16

12:30 Observed no precipitate, solution was clear