exp106

== =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) [|H NMR] (CD3OD, from exp047) [|H NMR] (CD3OD, from exp047) [|H NMR] (CD3OD, from exp054) [|H NMR] (CD3OD, from exp052)
 * 3,4-Dihydroxybenzaldehyde**
 * 5-Methylfurfuylamine**
 * Boc-Gly-OH**
 * tert-Butylisocyanide**

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]