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UC on ChemSpider
Alicia's Masters Thesis
Open Web Drug Dev.
To Do List
Ugi NMR Analysis
To optimize the reaction from
to make this
using Mettler Toledo's automated MiniMapper liquid handler and MiniBlock systems. Forty eight reactions are run in parallel using four reactants (2.0M in methanol) in different solvents / concentration.
Make up 2M methanol solutions (25mL each) of starting materials -
(8.759 g) and
(5.655 mL). The densities and m.w. data was obtained from the
The following are added in this order in a reaction tube equipped with a filtration frit
1) The additional solvent
2) The furfurylamine solution
3) The benzaldehyde solution
4) The boc-glycine solution
5) The tert-butyl isocyanide solution
6) The reaction mixture is placed in a shaker for 16 h then filtered
7) Two washed are performed by adding methanol (1 mL) followed by 15 min shaking then filter off
8) Product is dried under high vacuum
Parameters to modify:
concentration - 0.07M, 0.2M and 0.4M
reagent excess - 1.0 and 1.2 equivalents
solvent (for 0.2 and 0.71 conc only): ethanol, acetonitrile, THF
This is 48 experiments total and they are listed in this
The yields are listed in this
The results of this experiment were combined with
and reported in detail in
16:00 Made-up 2.0M solutions of Furfurylamine, benzaldehyde, Boc-glycine and t-butylisocyanide in methanol.
19:48 Minimapper started the run with the Red miniblock (1st priming with methanol, addition of methanol to first 18 slots, then priming with ethanol, addition of ethanol to the next 12 filter tubes, then priming with acetonitrile, addition of CH3CN to the next 12 filter tubes, then priming with THF, addition of THF to the last 6 filter tubes, then priming with methanol again, addition of the first reagent (amine) to all 48 tubes,wash canula with methanol, addition of benzaldehyde to all, wash canula with methanol, addition of boc-glycine to all tubes, wash canula with methanol and then addition of t-butyl isocyanide to all 48 filter tubes...and finally washing the canula with methanol.
21:11 Minimapper completed the addition of solvents and reagents to the miniblock.
21:12 Moved the miniblock on to the shaker set at 410rpm
21:12 Stopped the shaker and vacuumed off the solvent from the miniblock
21:20 Set the miniblock on the minimapper so that methanol (1mL) could be added to each filter tube for the first wash.
21:40 Placed the miniblock on to the shaker (600rpm)
21:51 Set the miniblock on the minimapper so that methanol (1mL) could be added to each filter tube for the second wash.
22:11 Removed from the minimapper and placed the miniblock on the shaker (600 rpm)
22:27 Vacuumed off the solvent from and placed the miniblock in desiccator connected to a high-vac.
10:30 Removed the miniblock from the desiccator and weighed the filter tubes.
InChI=1/C24H33N3O5/c1-23(2,3)26-21(29)20(17-11-8-7-9-12-17)27(16- 18-13-10-14-31-18)19(28)15-25-22(30)32-24(4,5)6/h7-14,20H,15-16H2 ,1-6H3,(H,25,30)(H,26,29)
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