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1 Electronic Supplementary Material (ESI) for New Journal of Chemistry. This journal is The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 205 A simple and greener approach for the amide bond formation employing FeCl 3 as a catalyst Basavaprabhu, M. Krishnamurthy, P. Nageswararao, V. Panduranga and Vommina V. Sureshbabu* # 09, Peptide Research Laboratory, Department of Studies in Chemistry, Central College Campus, Bangalore University, Dr. B. R. Ambedkar Veedhi, Bangalore , India hariccb@hotmail.com; hariccb@gmail.com; sureshbabuvommina@rediffmail.com. Supporting information Table of contents in supporting information S3.... General methods S3. Experimental [Typical procedure for the preparation of amides, 3a-l, 4] S3-S6 Characterization data for amides 3a-l, 4 S6. References for reported molecules S7 H NMR Spectrum of Compound 3a S C NMR Spectrum of Compound 3a S8.... H NMR Spectrum of Compound 3b S C NMR Spectrum of Compound 3b S9.... H NMR Spectrum of Compound 3c S C NMR Spectrum of Compound 3c S0.... H NMR Spectrum of Compound 3d S C NMR Spectrum of Compound 3d S.... H NMR Spectrum of Compound 3e S... 3 C NMR Spectrum of Compound 3e S2.... H NMR Spectrum of Compound 3f S
2 S C NMR Spectrum of Compound 3f S3.... H NMR Spectrum of Compound 3g S C NMR Spectrum of Compound 3g S4.... H NMR Spectrum of Compound 3h S C NMR Spectrum of Compound 3h S5.... H NMR Spectrum of Compound 3i S C NMR Spectrum of Compound 3i S6 H NMR Spectrum of Compound 3j S C NMR Spectrum of Compound 3j S7 H NMR Spectrum of Compound 3k S C NMR Spectrum of Compound 3k S8 H NMR Spectrum of Compound 3l S8.. 3 C NMR Spectrum of Compound 3l S9 H NMR Spectrum of Compound 4 S9.. 3 C NMR Spectrum of Compound 4 General information All solvents were freshly distilled before use. Melting points were determined using capillary method and are uncorrected. IR spectra were recorded on Schimadzu model FT-IR spectrophotometer (KBr pellets, 3 cm - resolution). H NMR and 3 C NMR spectra were recorded in CDCl 3 and DMSO on a Bruker AMX spectrometer using TMS as an internal standard. The RP-HPLC experiments were carried out in Agilent 00 series instrument having G3A VWD at λ = 254 nm for Fmoc compound, flow 0.5 ml/min, column: Agilent Eclipse XDB-C8, pore size-5μm, diameter x length = 4.6 x 50 mm; method: gradient 0.% TFA, water-acetonitrile system in 30 min. TLC experiments were done using MERCK TLC aluminium sheets (silica gel 60 F 254 ) and chromatograms were visualized by exposing in iodine chamber, UV-lamp or spraying with KMnO 4 and heating. Column chromatography was performed on neutral alumina and silica gel ( mesh) using ethyl acetate and hexane mixtures as eluent. S2
3 Experimental Section To a solution of acid (.0 mmol) in toluene (6 ml) was added 20 mol% FeCl 3 and an additional 0.5 eq of AcOH and the reaction mixture was allowed stir at 50 o C for 0-5 min. Then an amine (.0 mmol) in toluene (4 ml) was added to the above reaction mixture. The reaction mixture was refluxed at an elevated temperature till the completion of the reaction as monitored by TLC. Upon complete consumption of the starting materials, the reaction mixture was filtered and the filtrate was evaporated under reduced pressure. The crude product was extracted into EtOAc (5 ml). The EtOAc layer was then washed with 5% Na 2 CO 3 (5 ml), dil. HCl (5 ml), water (2 x 5 ml) and brine (5 ml). The organic layer was dried over anhydrous Na 2 SO 4 and the solvent was evaporated in vacuo to afford the crude which was then purified through silica gel column chromatography (EtOAc/hexane). Compound 3a: White solid (88 mg, 89%); mp 6-8 C (Lit. 8-9 C); H NMR (400 MHz, CDCl 3 ) δ 7.83 (br, H), 7.42 (d, J = 7.6 Hz, 2H), (m, 7H), (m, H), 3.63 (s, 2H); 3 C NMR (00 MHz, CDCl 3 ) δ 69.28, 37.68, 34.50, 29.53, 29.2, 28.95, 27.65, 24.49, 9.93, 44.79; IR (KBr) 3286, 2924, 659, 600, 535, 442 cm -. Compound 3b: White solid (80 mg, 80%); mp C (Lit C); H NMR (400 MHz, CDCl 3 ) δ 7.90 (d, J = 8 Hz, H), (m, 9H), 3.8 (s, 2H),.92 (s, 3H); 3 C NMR (00 MHz, CDCl 3 ) δ 68.07, 35.36, 32.82, 29.50, 29.05, 26.20, 26.7, 24.76, 24.46, 24.42, 9.99, 44.30, 22.7; IR (KBr) 334, 2926, 654, 59 cm -. Compound 3c: White solid (89 mg, 84%); mp C (Lit C); H NMR (400 MHz, CDCl 3 ) δ 7.78 (s, H), (m, 7H), 7.08 (d, J = 8.4 Hz, 2H), 3.68 (s, 2H), 2.32 (s, 3H); 3 C NMR (00 MHz, CDCl 3 ) δ 69.40, 35.22, 34.73, 34.09, 29.5, 29.4, 29.09, 27.50, 20.7, 44.60, 20.89; IR (KBr) 3332, 2926, 649, 60, 54, 46, 40 cm -. S3
4 Compound 3d: White solid (235 mg, 8%); mp C (Lit C); H NMR (400 MHz, CDCl 3 ) δ (m, 9H), 7.27 (br, H), 3.72 (s, 2H); 3 C NMR (00 MHz, CDCl 3 ) δ 69.05, 36.65, 34., 3.9, 29.56, 29.37, 27.87, 2.33, 7.06, 44.86; IR (KBr) 3346, 2927, 654, 596, 53, 458, 399 cm -. Compound 3e: White solid (204 mg, 83%); mp C (Lit C); H NMR (400 MHz, CDCl 3 ) δ (m, 8H), 7.22 (d, J = 8.8 Hz, 2H), 3.72 (s, 2H); 3 C NMR (00 MHz, CDCl 3 ) δ 69.4, 36.8, 34.7, 29.53, 29.46, 29.33, 28.95, 27.82, 2.08, 44.78; IR (KBr) 3345, 2925, 66, 63, 596, 506, 406, 349, 305 cm -. Compound 3f: White solid (205 mg, 85%); mp 7-9 C (Lit C); H NMR (400 MHz, CDCl 3 ) δ 7.44 (d, J = 8 Hz, 2H), (m, 4H), 7.2 (d, J = 7.6 Hz, 2H), 6.96 (d, J = 8.4 Hz, 2H), 3.85 (s, 3H), 3.70 (s, 2H); 3 C NMR (00 MHz, CDCl 3 ) δ 69.63, 59.2, 37.65, 30.72, 28.94, 26.33, 24.43, 9.80, 4.67, 55.34, 43.96; IR (KBr) 3289, 2928, 652, 542, 488, 302 cm -. Compound 3g: White solid (80 mg, 80%); mp C (Lit C); H NMR (400 MHz, CDCl 3 ) δ (m, 2H), (m, 8H), 3.7 (s, 2H), 2.39 (s, 3H); 3 C NMR (00 MHz, CDCl 3 ) δ 69.42, 37.65, 37.46, 3.30, 29.97, 29.48, 28.93, 24.43, 9.83, 44.49, 2.4; IR (KBr) 330, 2926, 660, 544,44, 389 cm -. Compound 3h: White solid (75 mg, 83%); mp o C (Lit C); H NMR (300 MHz, DMSO-d 6 ) δ 9.07 (s, H), 7.90 (d, J = 6.9 Hz, 2H), (m, 3 H), (m, 5H), 4.49 (d, J = 6.0 Hz, 2H); 3 C NMR (75 MHz, DMSO-d 6 ) δ 66.7, 39.79, 34.32, 3.23, 28.32, 28.27, 27.23, 27.8, 26.72, 42.54; IR (KBr) 330, 2926, 660, 544,44, 389, 254, 098, 049 cm -. S4
5 Compound 3i: White solid (85 mg, 82%); mp o C (Lit C); H NMR (300 MHz, DMSO-d 6 ) δ 0.6 (s, H), 7.88 (d, J = 8. Hz, 2H), 7.78 (d, J = 8. Hz, 2H), (m, 4H), 7.09 (t, J = 7.2 Hz, H), 4.22 (d, J = 6.0 Hz, 2H), 2.38 (s, 3H); 3 C NMR (75 MHz, DMSO-d 6 ) δ 65.36, 4.53, 39.27, 32.09, 28.89, 28.56, 27.69, 23.52, 20.34, 42.58, 2.00; IR (KBr) 3349, 2973, 660, 438, 389, 095, 050 cm -. Compound 3j: White solid (209 mg, 85%); mp o C (Lit C); H NMR (300 MHz, DMSO-d 6 ) δ 0.32 (s, H), 7.98 (d, J = 8.7 Hz, 2H), 7.76 (d, J = 8. Hz, 2H), 7.6 (d, J = 8.4 Hz, 2H), 7.36 (t, J = 7.8 Hz, 2H), 7.0 (t, J = 7.2 Hz, H), 4.09 (d, J = 6.0 Hz, 2H); 3 C NMR (75 MHz, DMSO-d 6 ) δ 64.4, 38.97, 36.38, 33.64, 29.6, 28.6, 28.43, 23.80, 20.4, 42.2; IR (KBr) 335, 292, 285, 653, 599, 463, 440 cm -. Compound 3k: White solid (82 mg, 8%); mp o C (Lit C); H NMR (300 MHz, DMSO-d 6 ) δ 0.2 (s, H), (m, 4H), (m, 4H), 7.09 (t, J = 7.5 Hz, H), 4.7 (s, 2H), 2.40 (s, 3H); 3 C NMR (75 MHz, DMSO-d 6 ) δ 65.69, 39.25, 37.69, 35.02, 32.2, 28.60, 28.28, 28.5, 24.83, 23.60, 20.33, 42.28, 20.98; IR (KBr) 3289, 2923, 65, 600, 535, 499, 44, 325 cm -. Compound 3l: Pale yellow solid (45 mg, 68%); mp o C (Lit o C); H NMR (300 MHz, DMSO-d 6 ) δ 9.93 (s, H), 7.57 (d, J = 8. Hz, 2 H), 7.28 (t, J = 7.5 Hz, 2 H), 7.02 (t, J = 7.2 Hz, H), 4.03 (s, 2 H); 3 C NMR (75 MHz, DMSO-d 6 ) δ 68.26, 39.33, 28.65, 22.94, 8.94, 40.05; IR (KBr) 3295, 2926, 669, 600, 547, 498, 442, 372, 39, 265 cm -. Fmoc-Aib-Aib-OMe, 4: White solid (284 mg, 67%); mp o C (Lit C); H NMR (300 MHz, CDCl 3 ) δ 7.77 (d, J = 7.2 Hz, 2H), 7.59 (d, J = 7.2 Hz, 2H), 7.40 (t, J = 7.2 Hz, 2H), 7.32(t, J = 7.2 Hz, 2H), 6.6 (br s, H), 5.38 (br s, H), 4.49 (d, J = 6.3 Hz, 2H), 4.9 (t, J = 6.3 S5
6 Hz, H), 3.62 (s, 3H),.45 (s, 2H); 3 C NMR (75 MHz, CDCl 3 ) δ 7.4, 54.90, 43.83, 4.34, 27.72, 27.05, 25.04, 24.9, 20.02, 65.93, 59.52, 54.8, 52.24, 47.43, 24.9; IR (KBr) 3294, 3245, 748, 709, 698, 548 cm -. References. Y. Wang, D. Zhu, L. Tang, S. Wang and Z. Wang, Angew. Chem. Int. Ed., 20, 50, M. Ramon, Synthesis,982, 4, Z. Zhang, Y. Yu and L. S. Liebeskind, Org. Lett., 2008, 0, D. P. Slobodan, J. Serbian Chem. Soc., 986, 5, L. L. Raffaella, Lett.Org. Chem., 2005, 2, K. Nagarajan, Ind. J. Chem. Sec. B: Organic Chemistry including Medicinal chemistry., 985, 24B, G. Irma, Ber. Der. Deutsch. Chem. Ges., 908, 40, K. V. Katkar, P. S. Chaudhari, K. G. Akamanchi, Green Chem., 20, 3, X. X. Shen, Q. Liu, R.G. Xing, B. Zhou, Catal. Lett., 2008, 26, M. Kunishima, Y. Watanabe, K. Terao, S. Tani, Eur. J. Org. Chem., 2004, R. Ferraccioli, A. Forni, Eur. J. Org. Chem., 2009, V. V. Sureshbabu, K. Ananda, Lett. Pept. Sci., 2000, 7, 4. S6
7 H NMR spectrum of compound 3a 3 C NMR spectrum of compound 3a S7
8 H NMR spectrum of compound 3b 3 C NMR spectrum of compound 3b S8
9 H NMR spectrum of compound 3c 3 C NMR spectrum of compound 3c S9
10 H NMR spectrum of compound 3d 3 C NMR spectrum of compound 3d S0
11 H NMR spectrum of compound 3e 3 C NMR spectrum of compound 3e S
12 H NMR spectrum of compound 3f 3 C NMR spectrum of compound 3f S2
13 H NMR spectrum of compound 3g 3 C NMR spectrum of compound 3g S3
14 H NMR spectrum of compound 3h 3 C NMR spectrum of compound 3h S4
15 H NMR spectrum of compound 3i 3 C NMR spectrum of compound 3i S5
16 H NMR spectrum of compound 3j 3 C NMR spectrum compound 3j S6
17 H NMR spectrum of compound 3k 3 C NMR spectrum of compound 3k S7
18 H NMR spectrum of compound 3l 3 C NMR spectrum of compound 3l S8
19 H NMR spectrum of compound 4 3 C NMR spectrum of compound 4 S9
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