Exp096

Researcher
David Bulger

Objective
Determine the solubility of [|Ugi Product 148B] from UC148, which also corresponds to 148B in the Isolated Compounds Sheet, in six solvents ([|methanol], [|ethanol], [|THF], [|acetonitrile], [|DMSO], [|toluene]).

Procedure
Make saturated solutions of Ugi Product 148B in the methanol, ethanol, THF, acetonitrile, DMSO, and toluene. Determine solubility using SAMS and internal standard (IS) methods.

NMR
[|ONSC096DN]**[what is the difference bewteen DN,DM and DR? JCB]** The solution from D3 was transferred into three different vials, which was transferred to three different NMR tubes with three different pipets. They are different in the transfer from vial D3 to NMR tube. [|ONSC096DM] [|ONSC096DR] [|ONSC096FN] [|ONSC096FM] [|ONSC096FR]

[|Raw JCAMP-DX File for ONSC096DN] [|Raw JCAMP-DX File for ONSC096DM] [|Raw JCAMP-DX File for ONSC096DR] [|Raw JCAMP-DX File for ONSC096FN] [|Raw JCAMP-DX File for ONSC096FM] [|Raw JCAMP-DX File for ONSC096FR]

Pictures
[|ONSC096-1] [|ONSC096-2][|ONSC096-3][|ONSC096-4]

Spreadsheets
[|ONSC096-1] [|ONSC096-2] media type="googlespreadsheet" key="rS70gmzVE08JZB5aYhzt-1Q" height="400" width="900"

Solubilities
Note: Need to make more Ugi Product to finish solubility measurements.
 * Vial || Solvent || SAMS Solubility (__M__) || IS Solubility (__M__) ||
 * ONSC096A || Methanol ||  ||   ||
 * ONSC096B || Ethanol ||  ||   ||
 * ONSC096C || THF ||  ||   ||
 * ONSC096D || Acetonitrile || 0.02, 0.02, 0.02 || 0.03, 0.04, 0.04 ||
 * ONSC096E || DMSO ||  ||   ||
 * ONSC096F || Toluene || 0.14, 0.14, 0.14 || 0.14, 0.16, 0.15 ||

Discussion
There was only enough Ugi Product to make saturated solutions in acetonitrile and toluene, which yielded solubilities of 0.02 __M__ and 0.14 __M__ respectively using SAMS and 0.03 __M__ and 0.14 __M__ respectively using IS.

Conclusion
Solubility of Ugi Product 148B in acetonitrile was found to be 0.02 __M__ and in toluene was found to be 0.14 __M__ using SAMS and 0.03 __M__ and 0.14 __M__ respectively using IS.

Log
2009-05-22 11:05 Labeled eight 1/2 dram vials (ONSC096A through ONSC096F) 11:08 Weighed vials 11:15 Added 900 uL of each solvent to respective vials and weighed 13:34 Added Ugi Product 216-7A to vials and weighed 13:45 Vortexed for 30 sec 13:47 Photo ([|ONSC096-1]) 13:49 Added Ugi Product to ONSC096A and ONSC096C 13:56 Added Ugi Product to ONSC096A (3.247 3 g) 13:58 Vortexed ONSC096A and ONSC096C for 30 sec 13:59 Photo of ONSC096A and ONSC096C ([|ONSC096-2]) 14:05 Began sonication (27 degrees Celsius) 14:35 Removed from sonicator (35 degrees Celsius) 14:38 Photo ([|ONSC096-3]) 17:13 Centrifuged for 3 min 17:19 Photo ([|ONSC096-4]) - only ONSC096D and ONSC096F are saturated 17:21 Transferred ONSC096D to D1 and ONSC096F to F1 (1/2 dram vial) 17:23 Centrifuged D1 and F1 for 3 min 17:25 Transferred D1 to D2 and F1 to F2 17:29 Centrifuged D2 and F2 for 3 min 17:30 Weighed D3 (2.446 2 g) and F3 (2.402 8 g) 17:33 Transferred D2 to D3 and F2 to F3 (1/2 dram vial) 17:36 Weighed D3 (2.729 4 g) and F3 (2.925 0 g) 17:40 Weighed vials: 17:50 Added 100 uL of D3 to DN, DM, and DR 17:51 Added 100 uL of F3 to FN, FM, and FR 17:52 Weighed vials: 17:56 Added 700 uL chloroform-d and weighed: Vortexed for 10 sec 6:13 Added 10 uL of 1,2-dichloroethane and weighed: Vortexed for 10 sec 20:40 Transferred solutions to NMR tubes with corresponding labels (ONSC096DN, ONSC096DM, ONSC096DR, ONSC096FN, ONSC096FM, ONSC096FR) 21:00 NMR ([|ONSC096DN]) 21:18 NMR ([|ONSC096DM]) 21:25 NMR ([|ONSC096DR]) 21:35 NMR ([|ONSC096FN]) 21:46 NMR ([|ONSC096FM]) 21:52 NMR ([|ONSC096FR])
 * Vial || Mass (g) ||
 * ONSC096A || 2.416 6 ||
 * ONSC096B || 2.434 3 ||
 * ONSC096C || 2.427 3 ||
 * ONSC096D || 2.405 8 ||
 * ONSC096E || 2.399 0 ||
 * ONSC096F || 2.416 2 ||
 * Vial || Solvent || Mass (g) ||
 * ONSC096A || Methanol || 3.159 1 ||
 * ONSC096B || Ethanol || 3.165 0 ||
 * ONSC096C || THF || 3.220 6 ||
 * ONSC096D || Acetonitrile || 3.135 0 ||
 * ONSC096E || DMSO || 3.398 0 ||
 * ONSC096F || Toluene || 3.219 0 ||
 * Vial || Mass (g) ||
 * ONSC096A || 3.175 7 ||
 * ONSC096B || 3.196 0 ||
 * ONSC096C || 3.246 2 ||
 * ONSC096D || 3.160 1 ||
 * ONSC096E || 3.443 9 ||
 * ONSC096F || 3.262 7 ||
 * Vial || Mass before addition (g) || Mass following addition (g) ||
 * ONSC096A || 3.175 7 || 3.181 2 ||
 * ONSC096C || 3.246 1 || 3.247 3 (Not enough Ugi product to saturate) ||
 * Vial || Mass (g) ||
 * DN || 2.399 0 ||
 * DM || 2.401 0 ||
 * DR || 2.437 3 ||
 * FN || 2.387 4 ||
 * FM || 2.407 9 ||
 * FR || 2.421 7 ||
 * Vial || Mass (g) ||
 * DN || 2.472 2 ||
 * DM || 2.475 6 ||
 * DR || 2.514 4 ||
 * FN || 2.472 5 ||
 * FM || 2.495 4 ||
 * FR || 2.509 0 ||
 * Vial || Mass (g) ||
 * DN || 2.545 8 ||
 * DM || 2.628 1 ||
 * DR || 2.662 1 ||
 * FN || 2.458 2 ||
 * FM || 2.653 0 ||
 * FR || 2.681 0 ||
 * Vial || Mass (g) ||
 * DN || 2.555 9 ||
 * DM || 2.635 7 ||
 * DR || 2.672 4 ||
 * FN || 2.467 5 ||
 * FM || 2.663 7 ||
 * FR || 2.694 3 ||