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Ugi NMR Analysis
To synthesize a
in methanol using Ugi 4CR.
A solution of
(212 uL, 2.09 mmol) and
(FFA) (235uL, 2.66 mmol )was prepared in methanol-d4 in a 4mL volumetric flask to form an imine overnight. The next day a solution of
(350 mg, 1.99 mmol), and
(240uL, 1.97 mmol) made up in a 4ml volumetric flask in methanol was added to the preformed imine. The product was filtered and washed with ice cold methanol (5mL).
Characterization of 108C
Colorless Crystals; M.pt 146-148C; HNMR (
ppm, CDCl3) 1.43 (s, 9H), 4.18 (m, 2H), 4.43 (m, 2H), 4.48 (s, 2H), 5.46 (s, 1H), 5.68 (s, 1H), 5.94 (s, 1H), 6.09 (m, 1H), 6.30 (s, 1H), 7.10-7.50 (m 11H) 13C NMR (
ppm, CDCl3) 28.3, 42.5, 42.8, 43.6, 63.0, 79.5, 107.9, 110.3, 110.8, 127.4, 127.6, 128.6, 128.7, 129.6, 134.2, 137.7, 142.0, 149.5, 155.7, 169.0, 170.3; FAB HRMS:
478.2366; calcd for C27H31N3O5 (M+H).
H NMR (CDCl3)
you also need spectrum in undeuterated methanol if you choose to monitor this way
[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 = 25min
No deuterated solvent added.
t = 17h 18min
spectrum way off scale - set methanol CH3 peak
t = 20h 34min
t = 5 days
t = 1week
(53mg / 800uL CDCl3)
A four component ugi reaction involving the imine of benzaldehyde and furfurylamine, and boc-glycine and benzyl isocyanide is only ~70% complete after one week, assuming the peak at 1.4 ppm (108B spectra) is the tert-butyl group.
The ugi product was successfully synthesized
19:35 Made up a solution of benzaldehyde and furfurylamine in methanol, in a 4 mL volumetric flask.This is
2005 Obtained an H NMR of 108A by removing 800uL of 108A in an NMR tube....spectrum obtained without an addition of any deuterated solvent.
12:53 Obtained H NMR of 108A (800uL) t = 17h18min
13:15 Made up a solution of benzyl isocyanide and Boc-glycine in a 4mL volumetric flask and added it to 108A, the preformed imine, this is
21:49 Obtained an H NMR of 108B (200uL in 600uL CD3OD)
14:00 Left the reaction mixture in a refrigerator.
15:00 Removed from the refrigerator.
13:18 Obtained an H NMR of 108B (200uL/600uL CD3OD) (t = 5days)
15:42 Obtained an H NMR of 108B (200uL/600uL CD3OD) (t = 1 week)
14:20 The reaction mixture did not develop any solid (usually seen with similar reactants). The erlenmeyer flask containing 108B was placed in a dry ice-acetone bath for one hour.
15:30 No solid had appeared even after placing the reaction mixture in dry ice acetone bath (-70C).
16:00 This is when some of the solvent was evaporated off with a gentle stream of N2.
16:20 Solid had appeared in the erlenmeyer flask containing 108B.
10:30 The solid was recrystallized from cold methanol (2ml). The product was dried under vacuum. The recovered mother liquor was saved for further crystallization (
16:20 A dry
-1 was obtained (192 mg)- [20.4% Yield]
20:23 Obtained HNMR of 108C by dissolving 53mg in CDCl3 (800uL).
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