Exp189scheme-i.jpg

Objective

To repeat the optimization reaction conducted in Exp189 to make this Ugi product using Mettler Toledo's automated Minimapper. Forty eight reactions are run in parallel using four reactant (2.0M in methanol) in different solvents / concentration.

Procedure

Make up 2M methanol solutions (50mL each) of starting materials - Benzaldehyde (10.550mL), Furfurylamine (8.837mL), Boc-glycine (17.518g) and tert-butyl isocyanide (11.310mL).
The following are added in this order in a reaction tube equipped with a filtration frit
1) The additional solvent (200uL methanol)
2) The benzaldehyde solution
3) The Furfurylamine solution
4) The Boc-Glycine solution
5) The tert-butyl isocycanide solution

Parameters to modify:
concentration - 0.5M, 0.25M and 0.1M
reagent excess - 1.0 and 1.2 equivalents
solvent (for 0.25 and 0.1 conc only): ethanol, acetonitrile, THF

This is 48 experiments total and they are listed in this spreadsheet

Results


Job file.

Discussion


Conclusion

The results are not meaningful because the liquid handler was not properly programmed.

Log

Log file1 , log file 2
2008-06-27
14:20 Moved the miniblock from the mapper to the shaker and started shaking (600rpm)
2008-06-28
15:30 Removed the miniblock from the shaker and drained excess solvents..
16:00 Added methanol (1mL) to each reaction tube and set it on the shaker
16:20 Removed from the shaker, drained methanol, added more methanol (1mL) to each reaction tube again and set the miniblock on the shaker..
16:50 Removed from the shaker and drained out methanol...left the miniblock connected to vacuum.
2008-06-29
13:00 Removed from vacuum and added dichloromethane (2mL) to each reaction tube in the miniblock.
13:30 Set the block again on the shaker.
17:00 Removed from the shaker and drained the solution of the product and dichloromethane in to collecting tubes, connected to vacuum, inorder to remove excess dichloromethane.
2008-06-30
15:00 Removed from under the house vac and placed it in a desiccator connected to a vacuum pump in ordesr to dry off the solvent completely.
19:00 Obtained the weights of the sample tubes with the products.

Tags


Compound
Inchi Key
Inchi
Furfurylamine
DDRPCXLAQZKBJP-UHFFFAOYAX
InChI=1/C5H7NO/c6-4-5-2-1-3-7-5/h1-3H,4,6H2
Benzaldehyde
HUMNYLRZRPPJDN-UHFFFAOYAE
InChI=1/C7H6O/c8-6-7-4-2-1-3-5-7/h1-6H
tert-butylisocynide
FAGLEPBREOXSAC-UHFFFAOYAL
InChI=1/C5H9N/c1-5(2,3)6-4/h1-3H3
Boc-Glycine
VRPJIFMKZZEXLR-UHFFFAOYAN
InChI=1/C7H13NO4/c1-7(2,3)12-6(11)8-4-5(9)10/h4H2,1-3H3,(H,8,11)(​H,9,10)
Ugi Product
BXAOUWIVXLQYOZ-UHFFFAOYAZ
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)