Exp230

Researcher
David Bulger

Objective
To synthesis four Ugi products in eight solvent at three concentrations.

Procedure
Using 96 well container as follows:
 * Ugi Product || Aldehyde || Primary Amine || Carboxylic Acid || Isocyanide ||
 * Known ([|**tert-butyl (2-{[2-(tert-butylamino)-2-oxo-1-phenylethyl(furan-2-ylmethyl)amino}-2-oxoethyl)carbamate**]]) || benzaldehyde || furfurylamine || boc-glycine || t-butylisocyanide ||
 * 230-1 || benzaldehyde || furfurylamine || boc-glycine || cyclohexylisocyanide ||
 * 230-2 || p-tolualdehyde || hexylamine || boc-glycine || t-butylisocyanide ||
 * 230-3 || p-tolualdehyde || hexylamine || boc-glycine || cyclohexylisocyanide ||
 * Wells || 1 (Known at 0.25M) || 2 (Known at 0.50M) || 3 (Known at 1.00M) || 4 (230-1 at 0.25M) || 5 (230-1 at 0.50M) || 6 (230-1 at 0.75M) || 7 (230-2 at 0.25M) || 8 (230-2 at 0.50M) || 9 (230-2 at 1.00M) || 10 (230-3 at 0.25M) || 11 (230-3 at 0.50M) || 12 (230-3 at 1.00M) ||
 * A - Ethanol ||  ||   ||   ||   ||   ||   ||   ||   ||   ||   ||   ||   ||
 * B - Methanol ||  ||   ||   ||   ||   ||   ||   ||   ||   ||   ||   ||   ||
 * C - THF ||  ||   ||   ||   ||   ||   ||   ||   ||   ||   ||   ||   ||
 * D - DMSO ||  ||   ||   ||   ||   ||   ||   ||   ||   ||   ||   ||   ||
 * E - DMF ||  ||   ||   ||   ||   ||   ||   ||   ||   ||   ||   ||   ||
 * F - Acetonitrile ||  ||   ||   ||   ||   ||   ||   ||   ||   ||   ||   ||   ||
 * G - Isopropanol ||  ||   ||   ||   ||   ||   ||   ||   ||   ||   ||   ||   ||
 * H - Chloroform ||  ||   ||   ||   ||   ||   ||   ||   ||   ||   ||   ||   ||

Pictures
[|UC230-1] [|UC230-2] [|UC230-3] [|UC230-4] [|UC230-5] [|UC230-6]

Spreadsheet
[|UC230-1] (General Spreadsheet with Calculations)**[note the wells only hold 300 microliters JCB]** media type="googlespreadsheet" key="r44RrDNuBMcy0EbEoJStzfw" height="400" width="900"

Conclusion

 * [As we discussed we learned some important things from this experiment - note them here JCB]**
 * [Most importantly it was not possible to properly seal the wells with the lid provided for aqueous experiments and solvents evaporated quickly. Also it was difficult to see which wells held precipitates. JCB]**

Improper sealing of the wells in this experiment allowed some problems to arise. As some of the solutions were volatile, the pressure unsealed the para-film covering allowing the solution to condense on the underside of the para-film. Once on the para-film, the solution appeared to travel across to the other wells tainting them. This resulted in the mixing of most of the solutions. In addition, some of the solutions such as chloroform dissolved the para-film. Furthermore, the amount of solution added to the wells exceeded the amount the wells could hold without overflowing. Overall, precipitation could not be distinguished from starting materials and the reaction mixtures contained large amounts of impurities.

Log
2009-05-26 18:46 Weighed 1-dram vials: 18:57 Added 0.219 0 g of boc-Glycine to each vial and weighed 19:40 Added 436 uL of solvent to vials 19:54 Vortexed each for 30 sec 20:00 Photo ([|UC230-1]) 20:01 Added 10.2 uL of benzaldehyde to wells (A-H)1-6 while parafilming following the addition to each row of wells 20:15 Added 11.8 uL of p-tolualdehyde to wells (A-H)7-12 while parafilming following the addition to each row of wells 20:25 Added 8.8 uL of furfurylamine to wells (A-H)1-6 while parafilming following the addition to each row of wells 20:40 Added 13.2 uL of hexylamine to wells (A-H)7-12 while parafilming following the addition to each row of wells 20:53 Photos ([|UC230-2], [|UC230-3]) - Note: Solvent seems to be evaporating from wells and parafilm doesn't seem to seal the wells very tightly 20:54 Added 50.0 uL of boc-Glycine solutions (AS-HS) as follows while parafilming following the addition to each row of wells: 21:20 Photos ([|UC230-4], [|UC230-5]) - Note: Solvent seems non-existant in some vials (only solid remaining) - evaporated solvent seems to be traveling along parafilm into some of the other wells (previously white wells on the right half becoming tainted yellow by the evaporation yellow solutino from the left wells) 21:21 Added 11.3 uL t-butyl isocyanide to (A-H)1-3 and (A-H)7-9 and added 12.4 uL cyclohexylisocyanide to (A-H)4-6 and (A-H)10-12 while parafilming following the addition to each row of wells 21:45 Added solvent to each of the wells as follows while parafilming following the addition to each row of wells: therefore Columns 4,7 and 10 aborted || 119 uL || 19 uL || Aborted || 114 uL || 14 uL || Aborted || 113 uL || 12.6 uL || 22:09 Photo ([|UC230-6]) and let sit with book on top of parafilmed wells
 * Vial || Mass (g) ||
 * AS || 5.101 5 ||
 * BS || 5.079 6 ||
 * CS || 5.130 2 ||
 * DS || 5.124 3 ||
 * ES || 5.112 0 ||
 * FS || 5.063 8 ||
 * GS || 5.103 8 ||
 * HS || 5.075 9 ||
 * Vial || Mass (g) ||
 * AS || 5.320 5 ||
 * BS || 5.298 7 ||
 * CS || 5.349 0 ||
 * DS || 5.342 9 ||
 * ES || 5.331 5 ||
 * FS || 5.283 6 ||
 * GS || 5.322 8 ||
 * HS || 5.294 9 ||
 * Vial || Solvent ||
 * AS || Ethanol ||
 * BS || Methanol ||
 * CS || THF ||
 * DS || DMSO ||
 * ES || DMF ||
 * FS || Acetonitrile ||
 * GS || Isopropanol ||
 * HS || Chloroform ||
 * Wells || Solution ||
 * A1-A12 || AS (ethanol) ||
 * B1-B12 || BS (methanol) ||
 * C1-C12 || CS (THF) ||
 * D1-D12 || DS (DMSO) ||
 * E1-E12 || ES (DMF) ||
 * F1-F12 || FS (Acetonitrile) ||
 * G1-G12 || GS (Isopropanol) ||
 * H1-H12 || HS (Chloroform) ||
 * Wells || 1 || 2 || 3 || 4 || 5 || 6 || 7 || 8 || 9 || 10 || 11 || 12) ||
 * A - Ethanol || 320 uL - this column overflowed the wells || 120 uL || 19.7 uL || Column 1 vials overflowed with solvent -
 * B - Methanol || 320 uL || 120 uL || 19.7 uL || Aborted || 119 uL || 19 uL || Aborted || 114 uL || 14 uL || Aborted || 113 uL || 12.6 uL ||
 * C - THF || 320 uL || 120 uL || 19.7 uL || Aborted || 119 uL || 19 uL || Aborted || 114 uL || 14 uL || Aborted || 113 uL || 12.6 uL ||
 * D - DMSO || 320 uL || 120 uL || 19.7 uL || Aborted || 119 uL || 19 uL || Aborted || 114 uL || 14 uL || Aborted || 113 uL || 12.6 uL ||
 * E - DMF || 320 uL || 120 uL || 19.7 uL || Aborted || 119 uL || 19 uL || Aborted || 114 uL || 14 uL || Aborted || 113 uL || 12.6 uL ||
 * F - Acetonitrile || 320 uL || 120 uL || 19.7 uL || Aborted || 119 uL || 19 uL || Aborted || 114 uL || 14 uL || Aborted || 113 uL || 12.6 uL ||
 * G - Isopropanol || 320 uL || 120 uL || 19.7 uL || Aborted || 119 uL || 19 uL || Aborted || 114 uL || 14 uL || Aborted || 113 uL || 12.6 uL ||
 * H - Chloroform || 320 uL || 120 uL || 19.7 uL || Aborted || 119 uL || 19 uL || Aborted || 114 uL || 14 uL || Aborted || 113 uL || 12.6 uL ||