Objective

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

Procedure

Three Ugi reactions were carried out in 1.5 ml eppendorf tubes labeled 1, 2 and 3. The labeled tube 1 contained methanol (500uL), octylamine (0.25mmol, 41.3uL), o-vanillin (0.25mmol, 38.04mg), Boc-Trp-OH (0.25mmol, 76.1mg), and butyl isocyanide (0.25mmol, 26.1uL), added in that order. Tube 2 contained methanol (500uL), octylamine (0.25mmol, 41.3uL), o-vanillin (0.25mmol, 38.04mg), Boc-Trp-OH (0.25mmol, 76.1mg), and 1-pentyl isocyanide (0.25mmol, 31.5uL), added in that order. Last, tube 3 contained methanol (500uL), octylamine (0.25mmol, 41.3uL), o-vanillin (0.25mmol, 38.04mg), Boc-Trp-OH (0.25mmol, 76.1mg), and benzyl isocyanide (0.25mmol, 30.4uL), added in that order.
After each addition the solution was vortexed for 15s and made sure a homogeneous solution was obtained. The Eppendorf tubes were left at room temperature.

Results


Discussion


Conclusion


Log

2007-08-16

16:00 Weighed Eppendorf tubes (Tube 1 - 0.8192g, Tube 2 - 0.8220g, Tube 3 - 0.8200g)
16:10 Added methanol (500uL) to both Eppendorf tubes
16:20 Weighed out o-vanillin (38.04mg)
16:30 Weighed out Boc-Trp-OH (76.1mg)
16:30 Added octylamine to each of the Eppendorf tubes, vortexed for 15s
16:35 Added o-vanillin to each of the tubes, vortexed for 15s
16:40 Added the Boc-Trp-OH, vortexed for 15s.
16:50 Added the isocyanides to each tube (Tube 1 - Butyl-isocyanide, Tube 2 - 1-Pentyl isocyanide, Tube 3 - Benzyl isocyanide), vortexed for 15-30s until everything dissolved
17:10 Let tubes sit undisturbed in fume hood

2007-08-17

10:30 Observed tubes, only tube 3 had a small amount of precipitate but dissolved when vortexed