Exp223

[[image:EXP223_rxn.png width="836" height="258"]]
media type="custom" key="3859769"

Objective
Synthesize of previously made 62E using [|piperonal], [|boc-glycine], [|t-butylisocyanide], and [|5-Methyl furfurylamine] in [|methanol].

Procedure
About 1 024 uL of methanol was added to one-half dram vial using Eppendorf pipet. Then piperonal, boc-glycine, t-butyl isocyanide, and 5-methylfurfurylamine was added in equimolar ratios (Eppendorf pipet for t-butyl isocyanide and 5-methylfurfurylamine) with 30-sec vortexing following each addition. The product was then washed in methanol at room temperature followed by dessication.

NMR
[|UCHEM223A] [|Raw UCHEM223A JCAMP-DX File] [|UCHEM223B] [|Raw UCHEM223B JCAMP-DX File]

Pictures
[|exp223_1a] [|exp223_1b] Note: The following photos are compressed. Higher resolution photos are available. [|223-2] [|223-3] [|223-4] [|223-5] [|223-6] [|223-7] [|223-8] [|223-9] [|223-10] [|223-11] [|223-12] [|223-13] [|223-14] [|223-15] [|223-16]

Spreadsheet
[|Usefulchem223] media type="googlespreadsheet" key="rfQ-kxhQc9Vbf5cfQU9bkcw" height="400" width="900"

Discussion
The yield was measured to be about 490% since the methanol had not completed evaporated. After more drying, the yield may be calculated. drying.

Conclusion
The yield was measured to be about 490%, most likely due to incomplete evaporation of the methanol.
 * [If NMR shows pure product report the yield JCB]**

2009-05-18
11.45 Added methanol (1 024 uL) to one-half dram screwcap vial (UC223.1) 11:52 Added piperonal (300.3 mg) 11:56 Vortexed for 30 sec 12:00 Added boc-glycine (350.4 mg) 12:06 Vortexed for 30 sec 12:08 Added t-butyl isocyanide (226 uL) 12:11 Vortexed for 30 sec 12:13 Added 5-methylfurfurylamine 12:14 Vortexed for 30 sec 12:24 Photo ([|exp223_1a]) 14:19 Photo ([|exp223_1b])

2009-05-19
9:51 Photo ([|223-2]) 9:52 Centrifuge for 2 min 9:58 Photo ([|223-3]) 9:59 Added about 1.5 mL of methanol with Pasteur pipet 10:00 Vortexed for 30 sec 10:01 Centrifuged for 2 min 10:05 Photo ([|223-4], [|223-5]) 10:05 Pipeted off supernatant (discarded) 10:08 Added about 1.5 mL of methanol 10:09 Vortexed for 30 sec 10:09 Centrifuged for 2 min 10:13 Photo ([|223-6]) 10:14 Centrifuged for 2 min 10:18 Photo ([|223-7]) 10:19 Pipeted off supernatant (discarded) 10:22 Mixed with spatula 10:23 Vortexed for 30 sec 10:24 Centrifuged for 2 min 10:27 Photo ([|223-8]) 10:28 Pipeted off superatant (discarded) 10:29 Added 700 uL of methanol with Eppendorf pipet 10:31 Vortexed for 30 sec 10:33 Centrifuged for 2 min 10:37 Photos ([|223-9], [|223-10]) 10:38 Pipetted off supernatant (discarded) 10:39 Added 700 uL of methanol 10:39 Vortexed for 30 sec 10:40 Centrifuged for 2 min 10:43 Room temperature checked (19 degrees Celsius) 10:44 Photo ([|223-11]) 10:45 Pipeted off supernatant (discarded) 10:46 Added 700 uL of methanol 10:47 Vortexed for 30 sec 10:48 Centrifuged for 2 min 10:51 Photo ([|223-12]) 10:52 Pipeted off supernatant (discarded) 10:54 Parafilmed and poked three holes in top with Pasteur pipet 10:55 Photo ([|223-13]) 10:56 Placed in dessicator 15:03 Connected vacuum to dessicator 19:02 Weighed vial with product (4.875 9 g) (Note: when vial is cleaned, the vial will be weighed empty to determine product mass) 19:22 Added product to NMR tube (223 DMSO-d6 - **[do you mean DMSO-d6? JCB]** yes, DMSO-d6) **[only use DMSO as a last resort because it is too difficult to remove JCB]** 19:29 Added 700 uL of DMSO to NMR tube - did not dissolve immediately 19:32 Added product and 700 uL of chloroform-d to another NMR tube (223 CDCl3) 19:33 Photos ([|223-14], [|223-15], [|223-16]) 21:00 Parafimed NMR tube

2009-05-20
12:20 NMR of [|UCHEM223A] 18:03 NMR of [|UCHEM223B]

Acknowledgements
The author wishes to thank Dr. Jean-Claude Bradley for the use of his lab and Khalid Mirza for help in setting up the experiment.