Skip to main content
Wikispaces Classroom is now free, social, and easier than ever.
Try it today.
Pages and Files
UC on ChemSpider
Alicia's Masters Thesis
Open Web Drug Dev.
To Do List
Ugi NMR Analysis
To synthesize a Ugi adduct(
in deuterated methanol.
Dissolved 3,4-dihydroxybenzaldehyde (2 mmol, 276 mg) and 5-methylfurfurylamine (2.2 mmol, 245 uL) in 4 mL CD3OD in a 4 mL volumetric flask, immediately transferred the contents to a 25mL Erlenmeyer flask, and removed 800 uL to obtain initial HMR spectra. The material used to obtain the H NMRs was returned to the Erlenmeyer, and the reaction was allowed to sit overnight 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 progression of the reaction was monitored by H NMR.
(*Spectra obtained on a Varian Inova 300 MHz instrument, unless specified otherwise)
63A (after aldehyde and amine)
(t=20 h 12 min)
63B (after boc-gly)
63C (after isonitrile)
(t=3 h, 41 min)
(t=25 h 44 min) (Varian 500 MHz H NMR, TMS peak referenced wrong because it was too faint)
Addition of isocyanide
note effect of adding boc-gly on imine/aldehyde/amine ratios and link to other experiments that did or did not demonstrate similar behavior
does it look like the Ugi product forms?
18:45 Dissolved 3,4-dihydroxybenzaldehyde in a minimal volume of CD3OD in a 4 mL volumetric flask. Added 5-methylfurfurylamine,
diluted to 4 mL, transferred to a 25 mL Erlenmeyer flask, swirled for 15 seconds, and immediately removed 800 uL for H NMR spectra (
18:59 Obtained H NMR spectra of imine mixture
19:15 Obtained H NMR spectra of imine mixture
19:38 Obtained H NMR spectra of imine mixture
15:08 Obtained spectra of imine mixture
(t=20h 12 min).
15:55 Added Boc-Gly-OH (
16:10 Obtained H NMR spectra of mixture
16:20 Added t-butylisocyanide (
16:46 Obtained H NMR spectra of mixture
16:53 Obtained H NMR spectra of mixture
17:06 Obtained H NMR spectra of mixture
17:20 Obtained H NMR spectra of mixture
20:41 Obtained H NMR spectra of mixture
(t=3h 41 min).
18:44 Obtained H NMR spectra of mixture
(t=25 h 44 min, on 500 MHz machine).
17:07 A small amount of solid had formed in the flask.
17:30 Added 250 uL hexanes and 250 uL chloroform to the solution and put on ice in to attempt to draw more solid from the solution.
18:00 Suction filtered through a Buechner funnel, rinsed with a minimal amount of cold methanol, to yield white crystals. Allowed filter paper and solid to dry with suction.
18:30 The weight of the crude crystals (on tared filter paper) was determined to be 30 mg.
22:00 Dissolved 63C in 1 mL CD3OD (didn't seem to dissolve), transferred 800 uL to a clean NMR tube.
22:20 Unable to obtain a good NMR, could not recover product, will attempt again in another experiment (
help on how to format text
Turn off "Getting Started"