exp054.gif

Objective

To synthesize a Ugi adduct(link) with 3,4-dihydroxybenzaldehyde, 5-methylfurfurylamine, tert-butylisocyanide and Boc-Gly-OH in methanol.

Procedure

This reaction was a repeat of exp063. 3,4-dihydroxybenzaldehyde (2 mmol, 276 mg) and 5-methylfurfurylamine (2.2 mmol, 245 uL) were dissolved in 4 mL MeOH in a 4 mL volumetric flask, immediately transferred the contents to a 1 dram vial. The material used to obtain the H NMRs was returned to the Erlenmeyer, and the reaction was allowed to sit 2 hours without stirring to preform the imine. Boc-Gly-OH (2 mmol, 350 mg) was added to the mixture, and the reaction was swirled for approximately 30 seconds in order to dissolve the reagent. After approximately 15 minutes, t-butyl isocyanide (2 mmol, 226 uL) was added to the mixture and swirled for approximately 30 seconds. The reaction was allowed to sit until solids began to precipitate from solution.

Results

(*Spectra obtained on a Varian Inova 300 MHz instrument, unless specified otherwise)
3,4-Dihydroxybenzaldehyde
H NMR (CD3OD, from exp047)
5-Methylfurfuylamine
H NMR (CD3OD, from exp047)
Boc-Gly-OH
H NMR (CD3OD, from exp054)
tert-Butylisocyanide
H NMR (CD3OD, from exp052)

Reaction Profiles


Discussion

Conclusion

Log


2007-03-27

Experiment repeated without obtaining NMR spectra of the reaction after additions of reagents. Performed reaction in a 1 dram vial, addition of reagents were repeated at the exact quantities and at the same time points.

2007-05-28

23:00 - Noted a significant amount of white solid has formed in the reaction vial.

2007-05-29

00:05 - Broke up the solid with a spatula, filtered the mixture, and rinsed with cold methanol. Resulting light tan solid was allowed to air dry for approx 10 min, placed in a vial, and placed in a dessicator (vial and cap tare: 6.0008 g) The filtrate was kept and allowed to evaporate.

2007-06-01



Tag

3,4-dihydroxybenzaldehyde
5-methylfurfurylamine
tert-butylisocyanide
Boc-Gly-OH