Exp195

=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. =Procedure= Make up 2M methanol solutions (25mL each) of starting materials - Furfurylamine (4.418mL), Boc-glycine (8.759g) and tert-butyl isocyanide (5.655mL) and [|2.077M] [|Benzaldehyde] (5.275mL ) in methanol. 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 - 0.5M, 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 Limiting reagent conc : 0.2mmol
 * Parameters to modify:**

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

[|Map file] ;

=Results= [|Job file].

=Discussion=

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

Log
[|Log file1] ;

10:00 Made-up 2M stock solutions (25mL) of Benzaldehyde, fufurylamine, boc-glycine, and t-butylisocyanide in methanol. 11:00 Weighed empty reaction tubes, weights noted in the spreadsheet. 16:50 Started running the minimapperl; to dispense the solvents and reactants to each reaction tube. 19:30 Minimapper completed additions to the reaction tubes, smoothly. 19:35 Set the miniblock on the shaker at 400 rpm. 15:30 Removed the miniblock from the shaker and vacuumed off excess solvent. 15:35 Set the miniblock on the minimapper and programmed it to deliver methanol (1mL) to each reaction tube. 15:50 Minimapper completed adding methanol to the reaction tubes. 15:51 Placed the miniblock on the shaker and started shaking at 400 rpm for 15 min. 16:05 Removed from the shaker and vacuumed off the solvent from the reaction tubes. 16:15 Set the miniblock on the minimapper and programmed it to deliver methanol (1mL) to each reaction tube for washing a second time. 16:35 Minimapper completed adding methanol to the reaction tubes. 16:36 Placed the miniblock on the shaker and started shaking at 400 rpm for 15 min. 16:51 Removed from the shaker and vacuumed off the solvent from the reaction tubes. The miniblock is let connected to the house vac for 30min. 17:21 The miniblock is disconnected from the house vac and placed in a desiccator connected to a high-vac. 20:50 Removed from the desiccator and weighed the dry filter tubes...realized that the tubes could still have been wet (weighed more than should have been) 21:20 Placed the miniblock in the desiccator connected to a high vac and left it for overnight drying. 09:20 Removed from the desiccator and weighed the dry filter tubes...the weights did not differ from the previous days weights.
 * 2008-07-09**
 * 2008-07-10**
 * 2008-07-11**

=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)] ||