Exp199

== =Objective= To optimize the reaction from Exp099 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. This run was verified by Tom Osborne. =Procedure= Make up 2M methanol solutions (25mL each) of starting materials - [|Benzaldehyde] (5.077mL ) Furfurylamine (4.418mL), Boc-glycine (8.759g) and tert-butyl isocyanide (5.655mL). 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

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
 * Parameters to modify:**

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

[|map file] =Results= [|job file] Yields listed in this [|spreadsheet]

=Discussion= Averaging over the 6 tubes for a given solvent/concentration, methanol 0.4M, methanol 0.2M, ethanol/methanol 60/40 0.2M and acetonitrile/methanol 60/40 0.2M give the best yields, while the lower concentration 0.07M for all solvents and THF/methanol 60/40 0.2M give the lower yields. =Conclusion= The results of this experiment will have to be verified to confirm there reproducibility.

Log
[|Log] 08:00 Made-up 2M solution of the starting materials in methanol. 11:20 Started the optimization run on Mettler Toledo's Minimapper. (Using Blue miniblock) 12:47 Minimapper completed liquid handling. 12:48 Removed the miniblock from the minimapper and placed it on the shaker (410rpm) 12:48 Shaker was turned off and the miniblock was removed from it. 12:50 Drained / Vacuumed off solvent from the filter tubes by performing a parallel filtration 13:00 Programmed the mini mapper to perform 1mL addition of methanol to each filter tube on the miniblock 13:25 Once addition of methanol was completed the miniblock was replaced on the shaker (600rpm) 13:40 Removed the miniblock from the shaker and drained/vacuumed off the solvent. 13:55 Programmed the mini mapper to perform 1mL addition of methanol to each filter tube on the miniblock for the second methanol wash 14:20 Once addition of methanol was completed the miniblock was replaced on the shaker (600rpm) 14:35 Removed the miniblock from the shaker and drained/vacuumed off the solvent, left the miniblock connected to the vacuum line. 15:15 The miniblock was removed from the vacuum line and placed in desiccator connected to high-vac.
 * 2008-07-12**
 * 2008-07-13**

=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)] ||