Objective

To synthesize one Ugi adduct following the EXPLAN005 . The compound will contribute toward a library for enoyl reductase inhibitors.

Procedure

A Ugi reaction was carried out in a 1 dram vial labeled 1. Vial 1 contained methanol (500uL), o-vanillin (0.5mmol, 76.1mg), hexylamine (0.5mmol, 50.6uL), Boc-Trp-OH (0.5mmol, 152.1mg), and benzyl isocyanide (0.5mmol, 60.9uL), added in that order.

Results

The results show that no precipitate was formed after 24 hours.

Discussion

This Ugi Product will be recorded as "No Precipitate Formed" on our records of tested Ugi products. Until further testing proves otherwise, we must assume this as a negative Ugi Reaction. In this experiment benzylisocyanide was the isonitrile component. Benzylisocyanide was the one isonitrile that was able to give precipitate up to this point. Meanwhile the aldehyde and acid components were o-vanillin and Boc-Trp-OH. These two components were suspected as being two of the components that don’t seem to work well together in precipitate formation. It turned out that no precipitate and no significant color change was observed one day post-experiment. This further suggested that o-vanillin and Boc-Trp-OH, while found in may compounds in the list of enoyl-reductase inhibitor, were having difficulty in forming precipitate. The results also placed doubt on the notion that benzylisocyanide may be an influential component for precipitate formation. After all, only one precipitate was noted and may just involve the combination of the components involved rather than any one specific component.

Conclusion

It is difficult to conclude anything from this experiment other than that this particular Ugi Reaction showed no success in forming a precipitate. There is no noticeable pattern as of now on which Ugi reactions will be positive and yield precipitates.
(No visual proof provided in the results section - experiment will have to be repeated showing pics immediately after mixing and several days later)

Log

2007-09-26

16:55: Weighed out o-Vanillin (76.1mg) directly into dram vial.
17:00: Weighed out Boc-Trp-OH (152.1mg) on weighing paper
17:06: Added methanol (500uL) into the dram vial, followed by 30 seconds vortexing.
17:10: Added amine into the dram vial, followed by 15 seconds vortexing.
17:15: Added acid into the dram vials, followed by 30 second vortexing.
17:20: Added isocyanide into the dram vials followed by 15 second vortexing.
17:22: Let vials sit in fume hood overnight

Tags

o-vanillin InChI=1/C5H11NS2.Na/c1-3-6(4-2)5(7)8;/h3-4H2,1-2H3,(H,7,8);/q;+1/p-1/fC5H10NS2.Na/q-1;m
Boc-trp-OH InChI=1/C16H20N2O4/c1-16(2,3)22-15(21)18-13(14(19)20)8-10-9-17-12-7-5-4-6-11(10)12/h4-7,9,13,17H,8H2,1-3H3,(H,18,21)(H,19,20)
hexylamine InChI=1/C6H15N/c1-2-3-4-5-6-7/h2-7H2,1H3
benzylisocyanide InChI=1/C8H7N/c1-9-7-8-5-3-2-4-6-8/h2-6H,7H2