Exp130-i.JPG
Comp ID
Aldehyde
Amine
Carboxylic Acid
Isocyanide
Ppt Yes/No
130-1
B-napthaldehyde (0.53mmol, 82.8mg)
5-methyl-furfurylamine (0.53mmol, 59.1uL)
formic acid (0.53mmol, 20.0uL)
n-butyl isocyanide (0.53mmol, 56.0uL)
No
130-2
B-napthaldehyde (0.53mmol, 82.8mg)
hexylamine (0.53mmol, 70.0 uL)
formic acid (0.53mmol, 20.0uL)
n-pentylisocyanide (0.53mmol, 66.7uL)
No
130-3
benzaldehyde (0.53mmol, 53.8 uL)
5-methyl-furfurylamine (0.53mmol, 59.1uL)
formic acid (0.53mmol, 20.0uL)
tosyl-methyl-isocyanide (0.53mmol, 103.5 mg)
No
130-4
B-napthaldehyde (0.53mmol, 82.8mg)
furfurylamine (0.53mmol, 46.8uL)
formic acid (0.53mmol, 20.0uL)
benzylisocyanide (0.53mmol, 64.4uL)
Yes
130-5
B-napthaldehyde (0.53mmol, 82.8mg)
furfurylamine (0.53mmol, 46.8uL)
formic acid (0.53mmol, 20.0uL)
n-butyl isocyanide (0.53mmol, 56.0uL)
No

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 dram vials labeled 1, 2, 3, 4, and 5. The labeled vial 1 contained methanol (500uL), B-napthaldehyde (0.53mmol, 82.8mg), 5-methyl-furfurylamine (0.53mmol, 59.1uL), formic acid (0.53mmol, 20.0uL), and n-butyl isocyanide (0.53mmol, 56.0uL), added in that order. Vial 2 contained methanol (500uL), B-napthaldehyde (0.53mmol, 82.8mg), hexylamine (0.53mmol, 70.0 uL), formic acid (0.53mmol, 20.0uL), and n-pentylisocyanide (0.53mmol, 66.7uL), added in that order. Vial 3 contained methanol (1mL), benzaldehyde (0.53mmol, 53.8 uL), 5-methyl-furfurylamine (0.53mmol, 59.1uL), formic acid (0.53mmol, 20.0uL), and tosyl-methyl-isocyanide (0.53mmol, 103.5 mg), added in that order. Vial 4 contained B-napthaldehyde (0.53mmol, 82.8mg), furfurylamine (0.53mmol, 46.8uL), formic acid (0.53mmol, 20.0uL), and benzylisocyanide (0.53mmol, 64.4uL), added in that order. Last, Vial 5 contained B-napthaldehyde (0.53mmol, 82.8mg), furfurylamine (0.53mmol, 46.8uL), formic acid (0.53mmol, 20.0uL), and n-butyl isocyanide (0.53mmol, 56.0uL), 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. The vials that did not show precipitate were placed on watch glasses. Two washes of 100uL of methanol were used to remove any product that remained in the tube.

Results


Picture of solutions soon after the addition of all components
experiment130before.JPG

Picture of solutions - next day.
experiment130after.JPG

Discussion

Dram vial 4 showed the formation of precipitate. The component that was specific to this vial was benzylisocyanide and future experimentation will be careful to see if this component is consistent in the formation of precipitate. Dram vial 3 was the only vial to show a significant color change (brown to black). The component specific to this vial was tosyl-methylisocyanide. We will be on the lookout in future experiments with tosyl-methyl isocyanide to see if similar color changes are shown.
Vials were not vortexed or sonicated prior to taking the picture one day after mixing. Sometimes this is required to induce precipitation.

Conclusion

Dram vial 4 was successful in the formation of precipitate and may be reproduced in the future and later isolated.

Log

2007-09-10

16:35: Added methanol (500uL) to dram vials 1, 2, 4, and 5. Added methanol (1mL) to dram vial 3.
16:38: Weighed out 2-naphthaldehyde for dram vial 1 (82.8mg)
16:41: Added 2-napthaldehyde into dram vial 1 followed by 30 seconds vortexing
16:44: Added 5-methyl-furfurylamine into dram vial 1 followed by 15 seconds vortexing.
16:46: Added formic acid into dram vial 1 followed by 15 seconds vortexing.
16:47: Added n-butylisocyanide into dram vial 1 followed by 15 seconds vortexing.
16:55: Weighed out 2-naphthaldehyde for dram vial 2 (82.8mg)
17:02: Added 2-napthaldehyde into dram vial 2 followed by 30 seconds vortexing
17:05: Added hexylamine into dram vial 2 followed by 15 seconds vortexing.
17:07: Added formic acid into dram vial 2 followed by 15 seconds vortexing.
17:09: Added n-pentylisocyanide into dram vial 2 followed by 15 seconds vortexing.
17:12: Weighed out tosyl-methyl-isocyanide for dram vial 3 (103.5mg)
17:18: Added benzaldehyde into dram vial 3 followed by 15 seconds vortexing
17:20: Added 5-methyl-furfurylamine into dram vial 3 followed by 15 seconds vortexing.
17:22: Added formic acid into dram vial 3 followed by 15 seconds vortexing.
17:24: Added tosyl-methyl-isocyanide into dram vial 3 followed by 30 seconds vortexing.
17:30: Weighed out 2-naphthaldehyde for dram vial 4 (82.8mg)
17:35: Added naphthalehyde into dram vial 4 followed by 30 seconds vortexing
17:39: Added furfurylamine into dram vial 4 followed by 15 seconds vortexing.
17:41: Added formic acid into dram vial 4 followed by 15 seconds vortexing.
17:42: Added benzylisocyanide into dram vial 4 followed by 15 seconds vortexing.
17:47: Weighed out 2-naphthaldehyde for dram vial 5 (82.8mg)
17:50: Added naphthalehyde into dram vial 5 followed by 30 seconds vortexing
17:53: Added furfurylamine into dram vial 5 followed by 15 seconds vortexing.
17:55: Added formic acid into dram vial 5 followed by 15 seconds vortexing.
17:57: Added n-butylisocyanide into dram vial 5 followed by 15 seconds vortexing.
18:00: Took Digital Still picture of all 5 vials.
18:03: Let vials sit in fume hood overnight.

2007-09-11

12:15: Precipitate was observed in dram vial 4. Dram vials 1, 2, 3, and 5 remained in solution.
12:30: Digital still was taken of the five dram vials.

2007-09-17

14:20: Transferred dram vials without precipitate (1, 2, 3, and 5) onto watch glasses to allow them to evaporate overnight.

Tags

B-naphthaldehyde InChI=1/C11H8O/c12-8-9-5-6-10-3-1-2-4-11(10)7-9/h1-8H
5-methyl-furfurylamine InChI=1/C6H9NO/c1-5-2-3-6(4-7)8-5/h2-3H,4,7H2,1H3
formic acid InChI=1/CH2O2/c2-1-3/h1H,(H,2,3)
n-butylisocyanide InChI=1/C5H9N/c1-3-4-5-6-2/h3-5H2,1H3
hexylamine InChI=1/C6H15N/c1-2-3-4-5-6-7/h2-7H2,1H3
n-pentylisocyanide InChI=1/C6H11N/c1-3-4-5-6-7-2/h3-6H2,1H3
benzaldehyde InChI=1/C7H6O/c8-6-7-4-2-1-3-5-7/h1-6H
furfurylamine InChI=1/C5H7NO/c6-4-5-2-1-3-7-5/h1-3H,4,6H2
benzylisocyanide InChI=1/C8H7N/c1-9-7-8-5-3-2-4-6-8/h2-6H,7H2
tosylmethylisocyanide InChI=1/C9H9NO2S/c1-8-3-5-9(6-4-8)13(11,12)7-10-2/h3-6H,7H2,1H3