Exp124-i.JPG

Objective

To synthesize two Ugi adducts. The compounds will contribute toward a library for enoyl reductase inhibitors.

Procedure

A solution of o-Vanillin (76.0mg, 0.5 mmol) and 5-methylfurfurylamine (55.7uL, 0.5 mmol) was prepared in methanol a 1ml volumetric flask to form an imine. After three hours Boc-Tryptophan (152.1mg, 0.5mmol), and 1-Butylisocyanide (52.3uL 0.5 mmol) was added to the preformed imine. The solution was left at room temperature overnight. A crystalline product obtained was centrifuges washed and recrystallized with methanol (5mL).
A solution of Veratraldehyde (83.0, 0.5 mmol) and 5-methylfurfurylamine (55.7uL, 0.5 mmol) was prepared in methanol a 1ml volumetric flask to form an imine. After three hours Boc-Tryptophan (152.17mg, 0.5mmol), and 1-Butylisocyanide (52.3uL 0.5 mmol) was added to the preformed imine. The solution was left at room temperature overnight. A crystalline product obtained was centrifuged, washed and recrystallized from methanol (5mL).

Results


o-Vanillin
HNMR
CNMR
5-methylfurfurylamine
H NMR
C NMR
Boc-Tryptophan
HNMR
CNMR
1-Butylisocyanide
HNMR
CNMR
Veratraldehyde
H NMR
C NMR


Conclusion

Experiment aborted.

Log

2007-08-16

15:52 Made up a solution of Veratraldehyde and 5-Methylfurfurylamine in methanol in a 1ml volumetric flask
15:52 Made up a solution of o-Vainillin and 5-Methylfurfurylamine in methanol in a 1ml volumetric flask.
19:02 Completed the addition of Boc-Tryptophan and n-butyl isocyanide.