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Researcher

Khalid Mirza & Jenna Mancinelli

Objective

To synthesize two Ugi products via a 4 component Ugi reaction.

Procedure

A 1M per component solution of 4-(trifluoromethyl) benzaldehyde (4mmol, 546.2uL), furfuryl amine (4mmol, 353.5uL), boc-glycine(700.7 mg, 4mmol), and an isocyanide (4 mmol) was made-up in a caluclated volume of methanol. Once a solid product was obtained, it was filtered and washed with methanol. The product was vacuum dried.
Charcterization of 235-1A :White solid; m.p. 172-174C;1H NMR (500MHz,external image delta.gif ppm, CDCl3) 1.33 (s, 9H), 1.44 (s, 9H), 4.23 (m, 2H), 4.49 (d, J=17.5Hz, 1H), 4.58 (d, J=17.5Hz, 1H), 5.42 (s, 1H), 5.71 (s, 1H), 5.91(s, 1H), 5.94 (s, 1H), 6.11 (s, 1H), 7.19 (s, 1H), phenyl 7.36 (d, J= 8.2 Hz, 2H), 7.50 (d, J=8.2Hz, 2H); 13C NMR ; (500MHz, external image delta.gif ppm, CDCl3) 28.25, 28.47, 42.62, 42.77, 51.77, 62.24, 79.66, 108.11, 110.47, 121.96, 125.30, 125.82, 129.57, 138.94, 142.04, 149.66, 155.66, 167.69, 170.36 ; IR (Ʋmax cm-1 ATR): 1650,1672,1697, 2969, 3329; FAB-HRMS -C25H32F3N3O5 m/z 512.236682 Da [M+H]+ , obtained xxxx.
Charcterization of 235-2A : White solid; m.p. 183-185C;1H NMR (500MHz,external image delta.gif ppm, CDCl3) 1.00-1.2 (m, 3H), 1.24-1.42 (m, 2H) 1.44 (s, 9H), 1.54-1.76 (m, 3H), 1.79-1.96 (m, 2H), 3.71-3.86 (m, 1H), 4.21 (s, 2H), 4.53 (d, J=17.5Hz, 1H), 4.57(d, J=17.5Hz, 1H), 5.42 (s, 1H), 5.77 (s, 1H), 5.93(s, 1H), 6.43 (m, 2H), 6.13 (s, 1H), 7.21 (s, 1H), phenyl 7.36 (d, J= 8 Hz, 2H), 7.50 (d, J=8 Hz, 2H); 13C NMR ; (500MHz, external image delta.gif ppm, CDCl3) 24.60, 24.65, 22.29, 28.19, 30.74, 32.56, 42.69, 42.55, 61.95, 79.60, 108.14, 110.42, 125.21, 129.48, 138.86, 142.01, 149.21, 155.65, 167.40, 170.41; IR (Ʋmax cm-1 ATR): 1325,1647,1687, 2935, 3382; FAB-HRMS - C27H34F3N3O5, m/z 538.252332 Da [M+H]+ , obtained xxxx.

Results

HNMR
235-1A
235-2A
CNMR
235-1A
235-2A
IR
235-1A
235-2A
Dept
235-1A
235-2A
MS FAB
235-1A Nominal
235-1A- HighRes
235-2A- Nomial
235-2A- HighRes
Mpt
235-1A - 172-174C
235-2A - 183-185C

Discussion

Conclusion

[You have enough to conclude JCB]

Log

2009-06-29

15:00 Labeled two vials: 235-1 and 235-2. Measured two boc-glycine (0.7007 g, 4mmol)
15:15 Pipetted appropriate amounts of 4-(trifluoromethyl)benzaldehyde (4mmol, 546.2uL) furfuryl amine (4mmol, 353.5uL) and methanol (2043.3uL to vial 235-1 and 1998.4uL to vial labeled 235-2) and into each vial. Added boc-glycine to each and vortexed for 15 seconds.
15:30 Added butylisocyanide (4mmol, 452.4uL) to vial 235-1 and added cyclohexylisocyanide (4mmol, 497.3uL) to vial 235-2. Vortexed again for 30 seconds. The final concentration per component in both solution is 1M.
15:33 Solid already beginning to form in vial 235-1.
16:30 Solids formed in both vials. Left to sit at room temperature.

2009-07-04

13:00 Filtered off the solids from vial 235-1 and 235-2 by vacuum filtration, washed the residue with methanol (3x 1mL)
14:30 White shiny crystalline substances obtained after washing was left to dry in a vacuum desiccator.
18:20 The dried solid obtained from vial 235-1 is now labeled 235-1A and the dried solid obtained from vial 235-2 is now labeled 235-2A.
18:30 Weighed 235-1A - 1.278g, yield 62.4%; 235-2A - 1.457g yield 67.7%;
18:45 Obtained HNMR of 235-1A and 235-2A

2009-07-07

10:00 Obtained a CNMR of 235-2A
14:00 Obtained melting points of 235-1A - 172-174C and 235-2A- 183-185C.

2009-07-08

13:00 Obtained CNMR and DEPT of 235-1A from an overnight run.