Exp235

=[add images and links to Chemspider JCB]= =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,[[image:http://pubs.acs.org/images/gifchars/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, [[image:http://pubs.acs.org/images/gifchars/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,[[image:http://pubs.acs.org/images/gifchars/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, [[image:http://pubs.acs.org/images/gifchars/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= [|235-1A] [|235-2A] [|235-1A] [|235-2A] [|235-1A] [|235-2A] [|235-1A] [|235-2A] 235-1A Nominal 235-1A- HighRes 235-2A- Nomial 235-2A- HighRes 235-1A - 172-174C 235-2A - 183-185C
 * HNMR**
 * CNMR**
 * IR**
 * Dept**
 * MS FAB**
 * Mpt**

=Discussion= =Conclusion= =Log=
 * [You have enough to conclude JCB]**

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.