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To Do List
Ugi NMR Analysis
To synthesize a
, tertbutylisocyanide and
in methanol using Ugi 4CR. This reaction is a reaction redone
A solution of
(veratradlehyde) (332 mg, 2 mmol) and f
(FFA) (234.8 uL, 2.2 mmol, 10% excess ) was prepared in methanol-d4 in a 2mL volumetric flask to form an imine. After two hours a solution of
(350 mg, 2 mmol), and
(226 uL, 2 mmol) madeup in a volumetric flask in methanol-d4 was added to the preformed imine. The product was filtered and washed with ice cold methanol (5mL) - The mother liquor was saved until it formed crystals again.
C26H37N3O7; White solid; 1H NMR (
ppm, CDCl3) 1.34 (s, 9H), 1.45 (s, 9H), 3.76 (s, 3H), 3.87 (s, 3H), 4.22 (s, 2H), 4.48 (s, 2H), 5.49-6.12 (m, 5H) 6.71-6.88 (m, 3H), 7.20 (s, 1H) 13C NMR (
ppm, CDCl3) 28.3, 28.5, 42.0, 42.8, 51.6, 55.7, 55.8, 62.5, 79.5, 107.4, 110.4, 110.7, 112.6, 122.0, 126.7, 141.7, 148.9, 149.9, 150.0, 155.6, 168.7, 170.2; HRMS (FAB,
calcd for C26H37N3O7 503.26, found 504.2725.
(Reactant NMRs from Exp054)
t = 17min
t = 24min
t = 32min
t = 34mim
t = 35min
t = 37min
t = 44min
t = 46min
t = 49min
t = 54min
t = 01h 00min
t = 01h 03min
t = 01h11min
t = 01h 16min
t = 01h 20min
t = 01h 23min
t = 01h 46min
t = 01h 53min
t = 02h 01min
t = 02h 08min
t = 02min
t = 03min
t = 05min
t = 07min
t = 15min
t = 20min
t = 23min
t = 48min
t = 51min
t = 01h 00min
t = 02h 03min
(Batch-1 : 86.3mg, batch-2: 33.8mg) -
you can't assume that 104C-2 is the same as 104C - need at least a separate HMR
C NMR (Image)
Ugi products obtained from veratraldehyde tend to be more powdery than crystalline and are relatively more soluble in methanol than there benzaldehyde counterparts.
A ugi product was successfully synthesized in 12% yield.
23:25 Madeup a solution of veratraldehyde and furfurylamine in 2 ml methanol-d4 in a volumetric flask to obtain
23:42 Obtained H NMR of 104A (t = 17min)
23:49 Obtained H NMR of 104A (t = 24min)
23:52 Obtained H NMR of 104A (t = 27min)
23:57 Obtained H NMR of 104A (t = 32min)
23:59 Obtained H NMR of 104A (t = 34min)
00:00 Obtained H NMR of 104A (t = 35min)
00:02 Obtained H NMR of 104A (t = 37min)
00:09 Obtained H NMR of 104A (t = 44min)
00:11 Obtained H NMR of 104A (t = 46min)
00:14 Obtained H NMR of 104A (t = 49min)
00:19 Obtained H NMR of 104A (t = 54min)
00:25 Obtained H NMR of 104A (t = 01h 00min)
00:28 Obtained H NMR of 104A (t = 01h 03min)
00:36 Obtained H NMR of 104A ( t= 01h 11min)
00:41 Obtained H NMR of 104A (t = 01h 16min)
00:45 Obtained H NMR of 104A (t = 01h 20min)
00:48 Obtained H NMR of 104A (t = 01h 23min)
01:00 Made up a solution of Boc-Glycine and
Butylisocyanide in a 2 mL volumetric flask in 2 mL methanol-d4.
01:11 Obtained C NMR of 104A (t = 01h 46min)
01:18 Obtained DEPT of 104A (t = 01h 53min)
01:26 Obtained H NMR of 104A (t = 02h 01min)
01:33 Obtained H NMR of 104A (t = 02h 08min)
01:37 Added the previously made solution of Boc Glycine and tert-butyl isocyanide in methanol-d4 to 104A in a centrifuge tube, to obtain
, 800uL of 104B was transferred back into the tube and the changes were monitored.
01:39 Obtained H NMR of 104B (t = 02min)
01:40 Obtained H NMR of 104B (t = 03min)
01:42 Obtained H NMR of 104B (t = 05min)
01:44 Obtained H NMR of 104B (t = 07min)
01:52 Obtained H NMR of 104B (t = 15min)
01:57 Obtained H NMR of 104B (t = 20min)
02:00 Obtained H NMR of 104B (t = 23min)
02:25 Obtained H NMR of 104B (t = 48min)
02:28 Obtained H NMR of 104B (t = 51min)
02:37 Obtained H NMR of 104B (t = 01h 00min)
03:40 Obtained H NMR of 104B (t = 02h 03min)
04:20 Solid had started to appear in the solution in the centrifiuge tube, at this time the solution from the NMR tube was poured into the centrifuge tube and set on a sonicator for 30min.
05:30 Almost the entire the solution in the centrifuge tube had solidified / looked like a white cake.
06:00 Removed the solid from the centrifuge tube into a beaker and rinsed out the centrifuge tube with methanol (2ml). The product in the beaker was set on a sonicator again and the enitre solid dissolved into it within a couple of minutes.
06:30 The beaker was parafilmed and left in the hood for crystallization.
13:00 Solid had appeared in the beaker with no traces of any methaol.
13:30 The solid in the beaker was removed from the beaker by using ice cold methanol (5ml) and the solvent was removed by filtering through a sintered glass funnel.
15:00 Obtained the solid
(86.3mg) after air drying, the mother liquor
was saved for further crystallization.
20:10 Obtained H NMR of 104C by dissolving 25 mg in 800uL of CDCl3.
09:28 Obtained a C NMR of 104C from an overnight run.
16:20 After filteration of 104D,
(33.8mg) of solid was obtained. Yield - 12%
The filtered mother liquor is
15:42 Obtained DEPT of 104C
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