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Ugi Reaction. Part V; N,N'-(4,4'-(ethane-1,2-diyl)bis(4,1-phenylene))bis(2-chloro-N-(2-(cyclohexylamino)-2-oxo-1-phenylethyl)acetamide)

SyntheticPage 796
DOI: 10.1039/SP796
Submitted Aug 19, 2015, published Aug 25, 2015
Sirin Gulten (siringulten@hotmail.com)
Reaction Scheme: <img src="/images/empty.gif" alt="" />Ugi Reaction<img src="/images/empty.gif" alt="" />. Part V

Chemicals Used

4,4'-Diaminobibenzyl (Fluka)

Benzaldehyde (Acros Organics)

Cyclohexyl isocyanide (Merck)

Chloroacetic acid (Fluka)

MeOH (Riedel-de Haën)

 

Procedure

A solution of 4,4'-diaminobibenzyl (0.94 mmol, 200 mg) in MeOH (7 mL) was treated with benzaldehyde (1.88 mmol, 0.19 mL), a solution of cyclohexyl isocyanide (1.88 mmol, 0.23 mL) in MeOH (3 mL), and chloroacetic acid (1.88 mmol, 178 mg) in the order given. The reaction mixture was stirred at room temperature for 24 hours, and then filtered. The precipitate was washed with first Et2O and then with n-hexane to remove unreacted reagents or by-products and dried to give cream coloured Ugi adduct (650 mg, 87%). m.p. 216-219oC, Rf(50%EtOAc/n-hexane): 0.50.

 

Author's Comments

The author thanks to NMR analysis Laboratory of Çanakkale Onsekiz Mart University for recording NMR spectra.

Data

IR-ATR: 3273, 3066, 3033, 2929, 2854, 1658, 1649, 701 cm-1; 1H NMR (400MHz, CDCl3): δ= 7.25-7.15 (14H, m, CHAr), 7.1 (4H, d, J=7.8 Hz, CHAr), 5.97 (2H, s, 2PhCH), 5.49 (2H, d, J=8.3 Hz, 2NH), 3.83-3.74 (6H, m, 2CH cyclohexyl and 2CH2Cl), 2.73 (4H, s, CH2CH2), 1.93-1.82 (4H, m, 2CH2 cyclohexyl), 1.68-1.58 (8H, m, 2CH2 cyclohexyl), 1.35-0.90 (8H, m, 4CH2 cyclohexyl) ppm; 13C NMR (100MHz, CDCl3): δ= 168.20 (Cq), 166.95 (Cq), 141.95 (Cq), 136.51 (Cq), 134.03 (Cq), 130.48 (CHAr), 130.29 (CHAr), 129.29 (CHAr), 128.77 (CHAr), 128.55 (CHAr), 65.65 (CH), 48.97 (CH), 42.69 (CH2), 37.26 (CH2), 32.90 (CH2), 32.86 (CH2), 25.52 (CH2), 24.92 (CH2), 24.84 (CH2) ppm.

 

Lead Reference

Marcaccini, S.; Pepino, R.; Pozo, M.C. Tetrahedron Lett. 2001, 42, 2727. doi: 10.1016/S0040-4039(01)00232.

Other References

Martins, M.B.; Carvalho, I. Tetrahedron, 2007, 63, 9923. doi:10.1016/j.tet.2007.04.105.

Supplementary Information

e.g. Actual NMR spectra (as images or jdx files for interactive spectra), photographs of apparatus, TLC’s or crystals or videos. Please contact the ChemSpider team (ChemSpider-at-rsc.org) for help with this.
Proton NMR 1 (Proton NMR 1.png)
Proton NMR 2 (Proton NMR 2.png)
Carbon NMR (Carbon.jpg)

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Keywords: addition, aldehydes, aromatics/arenes, carboxylic acids, elimination, Multicomponent reaction, nucleophilic, peptides, substitution