Objective

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

Procedure

Five Ugi reactions were carried out in 1.5 ml eppendorf tubes labeled 1, 2, 3, 4, and 5. The labeled tube 1 contained methanol (500uL), heptylamine (0.25mmol, 37.1uL), 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), heptylamine (0.25mmol, 37.1uL), o-vanillin (0.25mmol, 38.04mg), Boc-Trp-OH (0.25mmol, 76.1mg), and 1-pentyl isocyanide (0.25mmol, 31.5uL). Tube 3 contained methanol (500uL), heptylamine (0.25mmol, 37.1uL), o-vanillin (0.25mmol, 38.04mg), Boc-Trp-OH (0.25mmol, 76.1mg), and benzyl isocyanide (0.25mmol, 30.4uL). Tube 4 contained hexylamine (0.25mmol, 33uL), o-vanillin (0.25mmol, 38.04mg), Boc-Trp-OH (0.25mmol, 76.1mg), and butyl isocyanide (0.25mmol, 26.1uL). Last, tube 5 contained hexylamine (0.25mmol, 33uL), o-vanillin (0.25mmol, 38.04mg), Boc-Trp-OH (0.25mmol, 76.1mg), and 1-pentyl isocyanide (0.25mmol, 31.5uL).
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

2007-08-17

11:30 Weighed Eppendorf tubes (Tube 1 - 0.8157g, Tube 2 - 0.8168g, Tube 3 - 0.8277g, Tube 4 - 0.8256g, Tube 5 - 0.8380g)
11:40 Added methanol (500uL) to Eppendorf tubes
11:45 Weighed out o-vanillin (38.04mg)
11:55 Weighed out Boc-Trp-OH (76.1mg)
12:10 Added heptylamine (Tubes 1-3), hexylamine (Tubes 4-5), vortexed for 15s
12:20 Added o-vanillin to each of the tubes, vortexed for 15s
12:35 Added the Boc-Trp-OH, vortexed for 15s.
12:50 Added the isocyanides to each tube (Tubes 1,4 - Butyl-isocyanide, Tubes 2,5 - 1-Pentyl isocyanide, Tube 3 - Benzyl isocyanide), vortexed for 15-30s until everything dissolved
13:00 Let tubes sit undisturbed in fume hood

2007-08-20

13:00 All solutions were clear, no precipitates formed

add tags