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UC on ChemSpider
Alicia's Masters Thesis
Open Web Drug Dev.
To Do List
Ugi NMR Analysis
To cyclize a
to form a
Prepared 10% HCl solution by adding 100uL concentrated (12 M) aqueous HCl to 1mL volumetric flask. Diluted to mark with deuterated methanol. Took NMR spectra. Added 50mg Ugi Product (
) to NMR tube and monitored reaction via NMR spectra at specific intervals.
10% HCl Solution
10%HCl/ Ugi Product
TAR= 90 min
TAR= 150 min
1. The methyl group is still present at 2.2ppm.
2. It is hard to discern whether the boc group was lost even though a small peak at 1.6ppm begins to appear.
3. Some side reactions may be occuring with the appearance of new peaks at 1.29ppm - 1.38 ppm.
4. The doublets at 8.743 ppm and 4.477 point towards a clear
'. This is the first time this type of cleavage has ever been observed in 10% HCl.- Khalid
The Ugi product did not cyclize.
Fufuryl cleavage observed for the first time in a tertiary amide.
11:20 Set temperature bath to 65C. Prepared 10% HCL solution.
11:32 Attempted NMR spectra. Had problems getting the NMR to lock and spin consistently.
11:17 Prepared 800uL 10% HCl solution. Took NMR spectra. Set temperature bath to 65C.
12:01 Weighed out 50 mg of 62E and added it to contents of NMR tube.
12:15 Some problems with getting the crystals to dissolve. Added 20uL deuterated chloroform.
12:22 Crystals completely dissolved. Took NMR spectra.
12:46 Unable to get spectra until 12:37. Placed NMR tube in temperature bath. Bath temperature 60C.
12:52 Bath temperature 64C. Noticed condensation in the flask.
13:05 Bath temperature 70C. Reaction turned yellow.
13:30 Bath temperature 70C. Reaction turned orange. Took NMR spectra.
13:44 Bath temperature 70C. Returned reaction flask to temperature bath.
14:11 Bath temperature 70C. Took NMR spectra. Solution turned deep orange.
14:34 Bath temperature 70C. Placed NMR tube in bath.
15:30 Bath temperature 70C. Took NMR spectra. Solution turned red.
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