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Alicia's Masters Thesis
Open Web Drug Dev.
To Do List
Ugi NMR Analysis
To study the chemical interaction between N-(
-butoxycarbonyl) glycine and
-butyl isocyanide in Methanol-D4 by NMR spectroscopy.
One molar methanol-D4 solutions of
(113uL, 1mmol) and
(175mg, 1mmol) in CD3OD are prepared in separate 1 dram vials. 800uL of the solutions are used to obtain initial NMR spectra. Then 400uL of each solution is transfered to a clean nmr tube and shaken vigorously for a few seconds, the reaction is monitored by NMR spectra.
50A (Boc-Gly-OH +
t = 02min
t = 05min
t = 13min
t = 17min
t = 39min
t = 46min
t = 49min
t = 61min
t = 85min
t = 161min
t = 172 min
t = 322 min
t = 430min
t = 20h 21min
C NMR (Overnight run)
t = 24h 07min
From the overlays it is obvious that
-butyl isocyanide does not exhibit chemical reactivity towards Boc-Gly-OH.
All peaks in the starting materials remain unchanged over a 24 hours period .This is in sharp contrast to 2-morpholinoethyl isocyanide which looses its isonitrile identity in the presence of Boc-Gly-OH within a few minutes(
-butyl isocyanide like benzyl isocyanide (
) may be used as an isonitrile of choice for performing Ugi reactions involving Boc-Gly-OH.
11:00 - Obtained a 1H NMR and a 13C NMR of
14:20 - Added
14:22 - Obtained H NMR (t = 2min)
14:25 - Obtained H NMR (t = 5 min)
14:33 - Obtained C NMR (t = 13min)
14:37 - Obtained H NMR (t = 17min)
14:59 - Obtained C NMR (t = 39min)
15:06 - Obtained H NMR (t = 46min)
15:09 - Obtained H NMR ( t = 49min)
15:21 - Obtained H NMR (t = 61min)
15:45 - Obtained C NMR (t = 85min)
17:01 - Obtained C NMR (t = 161min)
17:12 - Obtained H NMR (t = 172min)
19:42 - Obtained H NMR (t = 322min)
21:30 - Obtained H NMR (t = 430min)
10:41 - Obtained C NMR(t = 20h 21min)
14:27 - Obtained H NMR (t = 24h 07min)
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