Exp203

== =Objective= To optimize the reaction from Exp099 to make this [|Ugi product] 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. =Procedure= Make up 2M methanol solutions (25mL each) of starting materials - [|benzaldehyde] (5.077 mL) [|furfurylamine] (4.418mL), [|boc-glycine] (8.759 g) and [|tert-butyl isocyanide] (5.655 mL). The densities and m.w. data was obtained from the [|Ugi Chemicals] table. 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 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 The 48 experiments are listed in this  [|spreadsheet] [|map file] C24H33N3O5; White solid; 1H NMR (500MHz, ppm, CDCl3) 1.33 (s, 9H), 1.45 (s, 9H), 4.21 (m, 2H), 4.49 (d, J=18Hz, 1H), 4.50 (d, J=18Hz, 1H), 5.47 (s, 1H), 5.60 (s, 1H), 5.62 (s, 1H), 5.89 (s, 1H), 6.10 (s, 1H), 7.19 (s, 1H), phenyl 7.21-7.37 (m, 5H)
 * Parameters to modify:**
 * Characterization of the Ugi Adduct from Exp 203A-11**

=Results= [|job file] The yields are reported in this  [|spreadsheet] [|Exp203A-11] [|Exp203B-10] [|Exp203C-07] [|Exp203D-12] [|Exp203F-10] [|Exp203H-12]
 * HNMR**

=Discussion= Based on the HNMR of the highest yield runs from each columns (except E and G which had very low yields) the Ugi products are pure. There has been some speculation that the peak at 1.6 ppm is an amide. However the since there is so little material in the EXP203C-07 NMR (based on the enormous CHCl3 peak at 7.27 ppm) and the 1.6 ppm peak is still very large, this is almost certainly water in the CDCl3.

=Conclusion= The results of this experiment were combined with Exp201 and Exp202 and reported in detail in Paper03.

Log
[|Minimapper Log] 16:00 Weighed the filter tubes for the run in a red miniblock 18:54 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. 20:17 Minimapper completed the addition of solvents and reagents to the miniblock. 20:20 Moved the miniblock on to the shaker set at 410rpm 20:20 Removed the miniblock from the shaker and performed a parallel filtration. 20:25 Placed the miniblock on the mapper and automate an addition of 1mL methanol 20:40 At the end of the addition, removed the miniblock and placed it on the shaker (600rpm) 20:50 Removed the shaker and performed a parallel filtration. 20:55 Placed the miniblock on the mapper and automate an addition of 1mL methanol for a second wash 21:10 At the end of the addition, removed the miniblock and placed it on the shaker (600rpm) 21:20 Removed the shaker and performed a parallel filtration on house vac. 21:50 Placed the miniblock in a desiccator connected to a high vac. 11: Removed the high vac and weighed the filter tubes for the product amounts.
 * 2008-07-19**
 * 2008-07-20**
 * 2008-07-21**

=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)] ||