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Alicia's Masters Thesis
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To Do List
Ugi NMR Analysis
To synthesize a
in methanol using Ugi 4CR.
A solution of
(106mg, 106uL, 1.04 mmol) and
(167mg, 1.01mmol) was prepared in methanol-d4 in a 1mL volumetric flask to form an imine overnight. The next day a solution of
(175 mg, 1 mmol), and
(120uL, 1mmol) made up in a 1ml volumetric flask in methanol was added to the preformed imine. The product was filtered and washed with ice cold methanol (5mL).
H NMR (CD3OD)
[CH2- 4.6 ppm (t) J=2.2Hz, aromatics- 7.3 - 7.4 ppm (broad multiplet)]
[CH2 (t)-46 ppm(J=28Hz), aromatics 127.9-134.5, Isonitrile Carbon (t)-157 ppm(J=22Hz)]
t = 3min
t = 4min
t = 11min
t = 37min
t = 44min
t = 1h15min
t = 2h 00min
t = 3h 4min
t = 17h 3min
t = 10min
The NMR and MS data confirms the formation of a Ugi product -
A Ugi product was isolated in 31% yield.
14:00 Made up a solution of 5-(Trifluoromethyl)-2-furylmethylamine (167mg) in methanol-d4 in a 1ml volumetric flask, transferred the solution to an NMR tube and obtained HNMR and CNMR.
17:46 Added benzaldehyde (106uL, 1mmol) to the NMR tube containing 1M solution of the amine, this is
17:49 Obtained HNMR of 109A (t = 3min)
17:50 Obtained HNMR of 109A (t = 4min)
18:01 Obtained HNMR of 109A (t = 11min)
18:23 Obtained HNMR of 109A (t = 37min)
18:30 Obtained HNMR of 109A (t = 44min)
19:01 Obtained HNMR of 109A (t = 01h15min)
19:46 Obtained HNMR of 109A (t = 02h)
20:50 Obtained HNMR of 109A (t = 03h 4min)
10:49 Obtained HNMR of 109A (t = 17h 3min)
13:45 Made up a solution of benzyl isocyanide (120uL, 1mmol) and Boc-Glycine (175mg, 1mmol) in CD3OD (1ml)
13:49 Added the isocyanide and amino acid solution in the NMR tube containing 109A to form
13:59 Obtained HNMR of 109B (t = 10min)
14:05 Soon after removing the NMR tube from the NMR instrument,
started to develop in the NMR tube.
19:20 Almost half of the NMR tube is now filled with the
17:25 After the entire nmr tube was filled with solid, the solid was forced out, washed with methanol, filtered through a sintered glass funnel. The obtained solid was air dried. The remaining mother liquor (
) was saved to recover more product.
19:30 A white solid product
(170mg) [31.16% yield] was obtained.
08:10 Obtained C NMR of 109C
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