Exp229

Objective
To synthesize two new Ugi Products.

Procedure
Based on the sortase inhibitor predictions in D-EXP016, two (D16-4 and D16-17) out of the top twenty Ugi products were picked for synthesis based on availability of reactants. In order to synthesize D16-4, 0.1 mmol each of N-boc-L-tryptophan, octadecylamine, p-tolualdehyde, and t-butylisocyanide were combined in methanol to create 0.15-mL final 0.75 __M__ solution. For D16-17, 0.1 mmol each of N-boc-L-tryptophan, hexylamine, benzaldehyde, and n-butylisocyanide were combined in methanol to create 0.10-mL final 1.00 __M__ solution. Final solutions were then sonicated for 35 min to stimulate crystal formation.

Pictures
[|UC229-1] [|UC229-2] [|UC229-3] [|UC229-4] [|UC229-5] [|UC229-6]

Spreadsheets
[|UCExp229] media type="googlespreadsheet" key="rWxiBT7Y83eUx2avaaf8cNg" height="400" width="700"

Conclusion
As no precipitate was observed in __ UC229-6 __, using 0.10-mL final 1.00 __M__ **[the [|CombiUgi sheet] calculates the final concentrations to be 0.67M - why the discrepancy? JCB]** solution for these ugi reactions does not seem feasible for synthesizing and precipitating the expected ugi products.

Log
16:40 Weighed 1-mL volumetric flask (15.582 6 g) 16:40 Added 0.304 1 g of N-boc-L-tryptophan to flask 17:13 Weighed (15.892 0 g) 17:26 Added 258.8 uL methanol to create 0.5 mL 2M solution 17:35 Vortexed for 30 sec 17:35 Sonicated (23 degrees Celsius) for 15 min 17:50 Photo ([|UC229-1]) 17:52 Temperature in sonicator is 29 degrees Celsius 18:15 Labeled flask (b-Try), vial for D16-4 Ugi Product (UC229-1), and vial for D16-17 Ugi Product (UC229-2) 18:16 Weighed vials 18:25 Added 11.8 uL of p-tolualdehyde to UC229-1 and weighed (2.421 5 g) 18:32 Added 33.2 mg of octadecylamine to UC229-1 and weighed (2.426 4 g) 18:35 Sample aborted as only 27.0 mg of octadecylamine should have been added 18:40 Vial UC229-1 cleaned and dried 18:50 Weighed empty vial UC229-1 (2.409 1 g) 18:51 Added 27.0 mg of octadecylamine to UC229-1 and weighed (2.436 9 g) 19:05 Added 11.8 uL of p-tolualdehyde to UC229-1 and weighed (2.448 2 g) 19:09 Added 22.0 uL of methanol to UC229-1 19:10 Vortexed for 10 sec 19:10 Added 22.0 uL of methanol to UC229-1 19:11 Vortexed for 10 sec 19:13 Added 50 uL of 2M N-boc-L-tryptophan solution to UC229-1 (Note: Khalid used same solution for Exp228 and had transferred solution to a 1-dram vial - although some evaporation of solvent did occur) 19:15 Vortexed about 3 min until solution was clear 19:21 Photo ([|UC229-2]) 19:22 Weighed (2.511 0 g) 19:25 Added 11.3 uL of t-butylisocyanide to UC229-1 19:26 Vortexed for 10 sec 19:27 Weighed (2.513 0 g) 19:28 Photo ([|UC229-3]) 19:29 Parafilmed UC229-1 19:31 Weighed vial UC229-2 (2.426 7 g) 19:32 Added 10.2 uL of benzaldehyde to UC229-2 and weighed (2.438 9 g) 19:34 Added 13.2 uL of hexylamine to UC229-2 - Note: Vial heated up and white vapor observed (possibly solvent evaporating) 19:36 Vortexed for 10 sec and weighed (2.448 2 g) 19:37 Added 50 uL of 2M N-boc-L-tryptophan solution to UC229-2 19:39 Vortexed for 10 sec and weighed (2.487 4 g) 19:40 Added 10.5 uL of n-butylisocyanide to UC229-2 and weighed (2.492 6 g) 19:45 Vortexed for 10 sec 19:45 Photo ([|UC229-4]) 19:46 Parafilmed UC229-2 19:47 Photo ([|UC229-5]) 19:55 Sonicated for 35 min (40 degrees Celsius) 20:48 Temperature in sonicator is 32 degrees Celsius - Note: Possibly cooled down during the 18 min following sonication. 20:48 Photo (__ UC229-6 __)
 * 5 May 2009**
 * Vial || Mass (g) ||
 * UC229-1 || 2.409 4 ||
 * UC229-2 || 2.427 3 ||