Exp130-i.JPG

Objective

To synthesize four different Ugi adducts following the EXPLAN005 . The compounds will contribute toward a library for enoyl reductase inhibitors. (link to specific library)
The densities in this table were obtained from Chemspider.com.
Comp ID/ Lib Rank
Aldehyde
Amine
Carboxylic Acid
Isocyanide
Ppt Yes/No
134-1
o-vanillin (0.5mmol, 76.1mg)
n-propylamine (0.5mmol, 29.5uL)
Boc-Trp-OH (0.5mmol, 152.1mg)
n-butylisocyanide (0.5mmol, 52.3uL)
No
134-2
o-vanillin (0.5mmol, 76.1mg)
n-propylamine (0.5mmol, 29.5uL)
Boc-Trp-OH (0.5mmol, 152.1mg)
n-pentylisocyanide (0.5mmol, 62.9 uL)
No
134-3
o-vanillin (0.5mmol, 76.1mg)
octylamine (0.5mmol, 82.6uL)
Boc-Trp-OH (0.5mmol, 152.1mg)
n-butylisocyanide (0.5mmol, 52.3uL)
No
134-4
o-vanillin (0.5mmol, 76.1mg)
octylamine (0.5mmol, 82.6uL)
Boc-Trp-OH (0.5mmol, 152.1mg)
n-pentylisocyanide (0.5mmol, 62.9 uL)
No

Procedure

Four Ugi reactions were carried out in 1 dram vials labeled 1, 2, 3, and 4. Vial 1 contained o-vanillin (0.5mmol, 76.1mg), n-propylamine (0.5mmol, 29.5uL), Boc-Trp-OH (0.5mmol, 152.1mg), and n-butylisocyanide (0.5mmol, 52.3uL), added in that order. Vial 2 contained o-Vanillin (0.5mmol, 76.1mg), n-propylamine (0.5mmol, 29.5uL), Boc-Trp-OH (0.5mmol, 152.1mg), and n-pentylisocyanide (0.5mmol, 62.9 uL), added in that order. Vial 3 contained o-Vanillin (0.5mmol, 76.1mg), octylamine (0.5mmol, 82.6uL), Boc-Trp-OH (0.5mmol, 152.1mg), and n-butylisocyanide (0.5mmol, 52.3uL), added in that order. Vial 4 contained o-Vanillin (0.5mmol, 76.1mg), octylamine (0.5mmol, 82.6uL), Boc-Trp-OH (0.5mmol, 152.1mg), and n-pentylisocyanide (0.5mmol, 62.9 uL), added in that order. After each addition, the solution was vortexed for 15s and made sure a homogeneous solution was obtained. The formation or absence of precipitate was noted. The dram vials were left at room temperature.

Results

Picture of solutions soon after the addition of all components
exp134before.JPG


Picture of solutions - next day
exp134after.JPG


Discussion

No precipitate was formed in any of the vials. These Ugi Products will be recorded as "No Precipitate Formed" on our records of tested Ugi products. Until further testing proves otherwise, we must assume these as negative Ugi Products.
Vials were not vortexed or sonicated prior to taking the picture one day after mixing. Sometimes this is required to induce precipitation.

Conclusion

It is difficult to conclude anything from this experiment other than that these particular compounds showed no success in forming a precipitate. There is no noticeable pattern as of now on which Ugi reactions will be positive and yield Ugi Products.

Log

2007-09-13

12:05: Weighed out o-Vanillin (76.1mg) directly into dram vials.
12:20: Weighed out Boc-Trp-OH (152.1mg) on weighing paper
12:32: Added methanol (500uL) into the dram vials, followed by 30 seconds vortexing.
12:38: Added amine into the dram vials, followed by 15 seconds vortexing.
12:41: Added acid into the dram vials, followed by 30 second vortexing.
12:45: Added isocyanide into the dram vials followed by 15 second vortexing
12:50: Took Digital Still picture of all 4 vials.
12:51: Let vials sit in fume hood overnight.

2007-09-13

13:30: Took Digital Still picture of all 4 vials.

2007-09-19

13:00: Transferred dram vials without precipitate (1, 2, 3, and 4) onto watch glasses to allow them to evaporate 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
propylamine InChI=1/C3H9N/c1-2-3-4/h2-4H2,1H3
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)
n-butylisocyanide InChI=1/C5H9N/c1-3-4-5-6-2/h3-5H2,1H3
octylamine InChI=1/C8H19N/c1-2-3-4-5-6-7-8-9/h2-9H2,1H3
n-pentylisocyanide InChI=1/C6H11N/c1-3-4-5-6-7-2/h3-6H2,1H3