Objective

To obtain a Ugi product using phenylacetaldehyde, 5-methylfurfurylamine, Boc-Gly-OH, and 2-morpholinoethyl isocyanide.

Procedure

To an NMR tube was added phenylacetaldehyde (111 uL, 1 mmol) and 5-methylfurfurylamine(111 uL, 1 mmol) and allowed to sit for 10minutes after mixing. Boc-Gly-OH (0.175 g, 1 mmol), 2-morpholinoethyl isocyanide (137 uL, 1 mmol) and CDCl3 (641 uL) were then added and mixed to bring volume to approximately 1mL.

Results

Characterization of 34A-T1 (6.5h)

HMR CMR

Discussion


Conclusion


Log

2006-10-23

13:10 Added phenylacetaldehyde and 5-methylfurfurylamine to NMR tube. Inverted NMR tube three times. Noticed a white solid beginning to form.
13:20 (t=10min) Added Boc-Gly-OH and 2-morpholinoethyl isocyanide along with CDCl3. White solid began to dissolve in solution. Inverted NMR tube three times.
19:45 Took proton and C13 NMRs 34A-T1 (6.5 h)

Tags

Phenylacetaldehyde, InChI=1/C8H8O/c9-7-6-8-4-2-1-3-5-8/h1-5,7H,6H2
Boc-Gly-OHInChI=1/C7H13NO4/c1-7(2,3)12-6(11)8-4-5(9)10/h4H2,1-3H3,(H,8,11)(H,9,10)
5-methylfurfurylamineInChI=1/C6H9NO/c1-5-2-3-6(4-7)8-5/h2-3H,4,7H2,1H3
2-morpholin ethyl isocyanideInChI=1/C7H12N2O/c1-8-2-3-9-4-6-10-7-5-9/h2-7H2
ugi034 InChI=1/C28H40N4O6/c1-21-10-11-23(37-21)20-32(25(33)19-30-27(35)38-28(2,3)4)24(18-22-8-6-5-7-9-22)26(34)29-12-13-31-14-16-36-17-15-31/h5-11,24H,12-20H2,1-4H3,(H,29,34)(H,30,35)