Exp121-vi.JPG

Objective

To synthesize a Ugi adduct from o-Vanillin, 5methyl furfurylamine Boc-tryptophan and 1-pentylisocyanide.

Procedure

A solution of o-Vanillin (76.05mg, 0.5 mmol) and 5-methylfurfurylamine (55.7uL, 0.5 mmol) was prepared in methanol-d4 in an 1ml volumetric flask to form an imine. Then Boc-Tryptophan (152.17mg, 0.5mmol), and 1-pentylisocyanide (62.9uL 0.5 mmol) was added to the preformed imine. The crystalline product was centrifuged, washed and recrystallized from methanol (5mL).
Characterization of 121ugi

Results

o-Vanillin
HNMR
CNMR
5-methylfurfurylamine
H NMR
C NMR
Boc-Tryptophan
HNMR
CNMR
1-pentylisocyanide
HNMR
CNMR
1-Butylisocyanide
HNMR
CNMR
121A
09min
24min
31min
41min
1h 2min
1h 33min
121B
16min
17h 52min


Conclusion

No Ugi product isolated

Log

2007-08-15

17:19 Madeup a solution of o-vanillin and 5-methyl furfurylamine in CD3OD in a 1ml volumetric flask, transferred to an NMR tube to form 121 A
17:28 Obtained HNMRs of 121A (09min)
17:45 Obtained HNMRs of 121A (24min)
17:50 Obtained HNMRs of 121A (31min)
18:00 Obtained HNMRs of 121A (41min)
18:21 Obtained HNMRs of 121A (1h 2min)
18:52 Obtained HNMRs of 121A (1h 33min)
19:10 Completed the addition of boc-tryptophan and pentyl isocyanide to give 121B
19:26 Obtained HNMR of 121B (16min)

2007-08-16

10:00 Solid has appeared in the solution of 121B
14:02 The solution in the NMR tube was shaken vigorously, the solid which had appeared dissolved...thereby allowing an HNMR tobe taken. (17h 52)

2007-08-17

10:00 Although there is some solid visible in the tube, but it may not isolable because of its mere quantity.

Tags

o-vanillin InChI=1/C5H11NS2.Na/c1-3-6(4-2)5(7)8;/h3-4H2,1-2H3,(H,7,8);/q;+1/p-1/fC5H10NS2.Na/q-1;m
5-methyl-furfurylamine InChI=1/C6H9NO/c1-5-2-3-6(4-7)8-5/h2-3H,4,7H2,1H3
Boc-trp-OH InChI=1/C16H20N2O4/c1-16(2,3)22-15(21)18-13(14(19)20)8-10-9-17-12-7-5-4-6-11(10)12/h4-7,9,13,17H,8H2,1-3H3,(H,18,21)(H,19,20)
n-butylisocyanide InChI=1/C5H9N/c1-3-4-5-6-2/h3-5H2,1H3
n-pentylisocyanide InChI=1/C6H11N/c1-3-4-5-6-7-2/h3-6H2,1H3