EXP223_rxn.png



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.

Results

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

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

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

Log

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.