Supporting Information
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- Ῥαφαὴλ Παπαδάκης
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1 Supporting Information Copyright Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim, 2014 One-Pot Decarboxylative Acylation of N-, O-, S-Nucleophiles and Peptides with 2,2-Disubstituted Malonic Acids Iryna O. Lebedyeva,* [a, b] Suvendu Biswas, [a] Kevin Goncalves, [a] Sean M. Sileno, [a] Ashton R. Jackson, [a] Kunal Patel, [a] Peter J. Steel, [c] and the late Prof. Dr. Alan R. Katritzky [a] chem_ _sm_miscellaneous_information.pdf
2 Contents Page Experimental Section... S2 References for the Supporting Information:... S10 1 H and 13 C Spectra of Decarboxylated Benzotriazolyl Intermediates 3a,b... S11 1 H and 13 C Spectra of Acylated N-, O-, S-Nucleophiles 5a-k... S12 1 H and 13 C Spectra of Acylated Amino Acids and Esters 7a g... S24 1 H and 13 C Spectra of Acylated Di- and Tripeptides 7h l... S31 S1
3 Experimental Section General Procedure for Synthesis of Decarboxylated Benzotriazolyl Intermediates 3a,b To a solution of 2,2-disubstitutedmalonic acid (1 mmol) in DMF (3 ml) 1-(methylsulfonyl)-1H-benzo[d][1,2,3]triazole (0.20 g, 1 mmol) was added followed by addition of TEA (0.21 ml, 1.5 mmol) and the mixture was subjected to microwave irradiation (20 W, 50 o C) for 1 h. On completion of the reaction the mixture was added to 4N HCl solution (50 ml) and extracted with ethyl acetate (3 x 30 ml). The organic layers were combined, washed with 4N HCl solution (2 x 50 ml) and sodium carbonate solution (2 x 50 ml), then dried over MgSO 4 and evaporated to give products 3a,b. 1-(1H-Benzo[d][1,2,3]triazol-1-yl)-2-methylpropan-1-one (3a). Yellow oil, 0.15 g, 89%, 1 H NMR (300 MHz, CDCl 3) δ 8.23 (t, J = 8.7 Hz, 1H), 8.06 (t, J = 8.7 Hz, 1H), 7.59 (d, J = 8.1 Hz, 1H), 7.44 (d, J = 8.1 Hz, 1H), (m, 1H), (m, 6H); 13 C NMR (75 MHz, CDCl 3) δ 176.8, 146.3, 131.5, 130.5, 126.2, 120.2, 114.7, 34.2, The obtained data matched those reported in literature. [1] ((1H-Benzo[d][1,2,3]triazol-1-yl)(cyclopentyl)methanone (3b). Light yellow oil, 0.17 g, 92%; 1 H NMR (300 MHz, CDCl 3) δ 8.22 (d, J = 7.8 Hz, 1H), 8.04 (d, J = 7.8 Hz, 1H), 7.57 (t, J = 7.2 Hz, 1H), 7.42 (t, J = 7.4 Hz, 1H), 4.19 (q, J = 7.5 Hz, 1H), (m, 2H), (m, 2H), (m, 4H); 13 C NMR (75 MHz, CDCl 3) δ 174.7, 146.2, 131.4, 130.2, 126.0, 120.1, 114.6, 44.2, 30.6, Anal. Calcd for C 12H 13N 3O: C, 66.96; H, 6.09; N, Found: C, 66.94; H, 6.27; N Acylated Amines (5 examples) 2-ethyl-N-propylbutanamide (5a). Colorless oil, 0.12 g, 75%; 1 H NMR (300 MHz, CDCl 3) δ 5.08 (brs, 1H), (m, 2H), (m, 2H), 1.73 (t, J = 6.3 Hz, 1H), (m, 4H), (m, 9H); 13 C NMR (75 MHz, CDCl 3) δ 157.0, 70.7, 42.6, 28.0, 23.2, 19.0, The obtained data matched those reported in literature. [2] S2
4 N-phenylcyclohexanecarboxamide (5b). White solid, 0.17 g, 84%, mp C; 1 H NMR (300 MHz, CDCl 3) δ 7.39 (d, J = 8.1 Hz, 2H), (m, 3H), 6.94 (t, J = 6.9 Hz, 1H), (m, 1H), (m, 7H), (m, 3H); 13 C NMR (75 MHz, CDCl 3) δ 174.5, 138.2, 129.0, 124.1, 119.9, 46.7, 29.8, 25.9, Anal. Calcd for C 13H 17NO: C, 76.81; H, 8,43; N, Found: C, 76.74; H, 8.64; N The obtained data matched those reported in literature. [3] N-Benzylisobutyramide (5c). White solid, 0.15 g, 83%, mp C; 1 H NMR (300 MHz, CD 3OD) δ (m, 5H), 6.51 (s, 1H), 3.99 (d, J = 4.8 Hz, 2H), (m, 1H), 1.10 (d, J = 6.6 Hz, 6H); 13 C NMR (75 MHz, CDCl 3) δ 177.2, 138.6, 128.7, 127.7, 127.5, 43.5, 35.7, The obtained data matched those reported in literature. [4] N-Benzylcyclohexanecarboxamide (5d). White solid, 0.17 g, 78%, mp C; 1 H NMR (300 MHz, CDCl 3) δ (m, 5H), 5.71 (d, J = 7.5 Hz, 1H), 4.40 (d, J = 5.7 Hz, 2H), 2.07 (t, J = 11.7 Hz, 1H), (m, 5H), (m, 5H); 13 C NMR (75 MHz, CDCl 3) δ 176.1, 133.3, 128.9, 127.9, 127.6, 67.3, 45.8, 43.6, 29.9, The obtained data matched those reported in literature. [5] N-(2,6-Dimethylphenyl)cyclopropanecarboxamide (5e). White solid, 0.16 g, 83%, mp C; 1 H NMR (300 MHz, CD 3OD) δ 7.07 (s, 3H), 2.20 (s, 6H), (m, 1H), 0.94 (d, J = 7.2 Hz, 2H), 0.85 (d, J = 7.8 Hz, 2H); 13 C NMR (75 MHz, CD 3OD) δ 175.4, 137.1, 135.9, 129.1, 128.3, 18.5, 14.9, 7.6; Anal. Calcd for C 12H 15NO: C, 76.16; H, 7.99; N, Found: C, 76.30; H, 8.22; N The obtained data matched those reported in literature. [6] S3
5 Acylated Alcohols (3 examples) Phenyl cyclopentanecarboxylate (5f). Colorless oil, 0.16 g, 86%; 1 H NMR (300 MHz, CDCl 3) δ 7.35 (d, J = 6.6 Hz, 2H), (m, 1H), 7.07 (d, J = 7.5 Hz, 2H), (m, 1H), (m, 5H), (m, 3H); 13 C NMR (75 MHz, CDCl 3) δ 174.0, 150.9, 129.5, 125.8, 121.6, 38.3, 25.5, The obtained data matched those reported in literature. [7] (1R,2S,5R)-2-Isopropyl-5-methylcyclohexyl cyclohexanecarboxylate (5g). Colorless oil, 0.22 g, 81%; 20 [α] D = 30.0 (c 1.0, CH 3OH); 1 H NMR (300 MHz, CDCl 3) δ (m, 1H), 2.26 (t, J = 10.8 Hz, 1H), (m, 1H), (m, 3H), (m, 5H), (m, 7H); (m, 9H), 0.75 (d, J = 6.6 Hz, 3H); 13 C NMR (75 MHz, CDCl 3) δ 181.7, 71.8, 50.1, 45.0, 43.1, 34.7, 31.8, 29.0, 25.9, 25.5, 23.2, 22.4, 21.2, The obtained data matched those reported in literature. [8] 3S,8S,9S,10R,13R,14S,17R)-10,13-Dimethyl-17-((R)-6-methylheptan-2-yl)- 2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-3-yl 2-ethylbutanoate (5h). White 20 semisolid, 0.37 g, 77%, mp; [α] D = 11.0 (c 1.0, CH 3OH); 1 H NMR (300 MHz, DMSO-d 6) δ 5.21 (t, J = 6.6 Hz, 1H), (m, 1H), (m, 54H); 13 C NMR (75 MHz, CDCl 3) δ 170.8, 140.9, 121.9, 75.6, 72.0, 57.0, 56.3, 50.3, 49.0, 42.5, 42.4, 40.0, 39.7, 37.5, 36.4, 36.0, 32.1, 31.8, 28.4, 28.2, 27.8, 24.6, 24.0, 23.0, 22.8, 21.3, 19.6, 19.0, 12.1, The obtained data matched those reported in literature. [9] S4
6 Acylated Thioalcohols (3 examples) S-Phenyl cyclopentanecarbothioate (5i). Yellow oil, 0.18 g, 88%; 1 H NMR (300 MHz, CDCl 3) δ (m, 5H), 3.03 (t, J = 8.4 Hz, 1H), (m, 4H), (m, 4H); 13 C NMR (75 MHz, CDCl 3) δ 200.9, 134.9, 134.6, 129.2, 128.3, 53.0, 30.8, The obtained data matched those reported in literature. [10] N-(Tert-butoxycarbonyl)-S-(cyclopropanecarbonyl)-L-cysteine (5j).Yellow oil, 0.24 g, 83%; 20 [α] D = 17.0 (c 1.0, CH 3OH); 1 H NMR (300 MHz, CDCl 3) δ 9.77 (s, 1H), 5.35 (d, J = 7.8 Hz, 1H), (m, 1H), (m, 1H), (m, 2H), 1.36 (s, 9H), 1.09 (t, J = 5.0 Hz, 2H), 0.90 (t, J = 3.8 Hz, 2H); 13 C NMR (75 MHz, CDCl 3) δ 199.1, 174.3, 155.7, 80.6, 53.5, 30.8, 28.4, 22.9, 11.4; Anal. Calcd for C 12H 19NO 5S: C, 49.81; H, 6.62; N, Found: C, 49.86; H, 7.00; N N-((Benzyloxy)carbonyl)-S-(cyclobutanecarbonyl)-L-cysteine (5k). Yellow oil, 0.28 g, 80%; 20 [α] D = 22.0 (c 1.0, CH 3OH); 1 H NMR (300 MHz, CDCl 3) δ (m, 5H), 6.72 (br s, 1H), 5.03 (d, J = 12.6 Hz, 2H), (m, 1H), (m, 2H), (m, 4H), (m, 5H); 13 C NMR (75 MHz, CDCl 3) δ 201.4, 174.0, 156.3, 136.2, 128.7, 128.4, 128.3, 67.5, 54.0, 46.9, 29.9, 26.1, 18.2; HRMS (ESI) C 17H 21NO 5SNa calcd.: [(M+Na) + ] = found: [(M+Na) + ] = Acylated Aminoacids (8 examples) Benzyl isobutyrylglycinate (7a). White solid, 0.14 g, 80%, mp C; 1 H NMR (300 MHz, CDCl 3) δ (m, 5H), 6.04 (br s, 1H), 5.16 (s, 2H), 4.06 (d, J = 5.1 Hz, 2H), (m, 1H), 1.15 (d, S5
7 J = 6.9 Hz, 6H); 13 C NMR (75 MHz, CDCl 3) δ 177.3, 170.2, 135.3, 128.8, 128.7, 128.5, 67.4, 41.5, 35.5, 19.6; HRMS (ESI) C 13H 18NO 3 calcd.: [(M+H) + ] = found: [(M+H) + ] = Benzyl (cyclobutanecarbonyl)glycinate (7b). White solid, 0.20 g, 86%, mp C; 1 H NMR (300 MHz, CDCl 3) δ (m, 5H), (m, 1H), 5.14 (s, 2H), 4.04 (d, J = 4.5 Hz, 2H), (m, 1H), (m, 4H), (m, 2H); 13 C NMR (75 MHz, CDCl 3) δ 175.3, 170.2, 135.3, 128.8, 128.7, 128.5, 67.4, 41.5, 39.8, 25.5, 18.4; Anal. Calcd for C 14H 17NO 3: C, 68.00; H, 6.93; N, Found: C, 68.12; H, 6.99; N (Cyclopropanecarbonyl)-L-leucine (7c). White solid, 0.16 g, 79%, mp C; [α] D = 12.0 (c 1.0, CH 3OH); 1 H NMR (300 MHz, CDCl 3) δ 9.87 (s, 1H), 7.04 (d, J = 10.8 Hz, 1H), (m, 1H), (m, 3H), (m, 1H), (m, 10H); 13 C NMR (75 MHz, CDCl 3) δ 176.4, 175.1, 51.4, 41.3, 25.0, 23.0, 22.0, 14.8, 7.9. The obtained data matched those reported in literature. [11] 20 (2-Ethylbutanoyl)-L-valine (7d). White solid, 0.17 g, 85%, mp C; [α] D = 14.0 (c 1.0, CH 3OH); 1 H NMR (300 MHz, CDCl 3) δ 6.00 (d, J = 7.8 Hz, 1H), (m, 1H), (m, 1H), (m, 5H), (m, 2H), 0.98 (d, J = 6.9 Hz, 3H), 0.95 (d, J = 6.6 Hz, 3H); 13 C NMR (75 MHz, CDCl 3) δ 176.0, 175.3, 57.2, 40.0, 31.2, 25.7, 25.5, 19.2, 18.4, 17.9; Anal. Calcd for C 11H 21NO 3: C, 61.37; H, 9.83; N, Found: C, 61.41; H, 10.04; N (2-Ethylbutanoyl)-L-phenylalanine (7e). White solid, 0.21 g, 80%, mp C; [α] D 20 = (c 1.0, CH 3OH); 1 H NMR (300 MHz, CD 3OD) δ (m, 5H), (m, 1H), (m, 1H), 2.92 (dd, J = 17.1, 10.2 Hz, 1H), (m, 1H), (m, 4H), 0.85 (t, J = 7.5 Hz, 3H), 0.58 (t, J = 7.5 Hz, 3H); 13 C NMR (75 S6
8 MHz, CDCl 3) δ 176.9, 174.8, 136.0, 129.5, 128.7, 127.3, 53.1, 51.2, 37.8, 25.8, 12.0; Anal. Calcd for C 15H 21NO 3: C, 68.42; H, 8.04; N, Found: C, 68.18; H, 8.28; N (2-Ethylbutanoyl)-D-phenylalanine (7f). White solid, 0.22 g, 84%, mp C; [α] D = 20.0 (c 1.0, CH 3OH); 1 H NMR (300 MHz, CD 3OD) δ (m, 5H), (m, 1H), 3.21 (dd, J = 14.1, 4.8 Hz, 1H), 2.88 (dd, J = 14.1, 10.3 Hz, 1H), (m, 1H), (m, 4H), 0.81 (t, J = 7.5 Hz, 3H), 0.54 (t, J = 7.5 Hz, 3H); 13 C NMR (75 MHz, CD 3OD) δ 178.7, 175.0, 138.8, 130.3, 129.5, 127.8, 54.8, 51.7, 38.5, 27.2, 12.5; Anal. Calcd for C 15H 21NO 3: C, 68.42; H, 8.04; N, Found: C, 68.47; H, 8.17; N (2-Ethylbutanoyl)-D,L-phenylalanine (7g). White solid, 0.23 g, 87%, mp C; 1 H NMR (300 MHz, CDCl 3) δ (br s, 1H), (m, 5H), (m, 1H), (m, 1H), (m, 2H), (m, 1H), (m, 4H), (m, 6H); 13 C NMR (75 MHz, CDCl 3) δ 177.0, 175.0, 135.9, 129.4, 128.7, 127.3, 53.1, 51.2, 37.7, 25.6, The obtained data matched those reported in literature. [12] Acylated Di- and Tripeptides (5 examples) (Cyclobutanecarbonyl)-L-leucyl-L-alanine (7h). White solid, 0.25 g, 89%, mp C; 20 [α] D = 9.0 (c 1.0, CH 3OH); 1 H NMR (300 MHz, CDCl 3) δ (br s, 1H), 6.17 (s, 1H), (m, 1H), 2.31 (t, J = 10.9 Hz, 1H), 2.13 (t, J = 10.8 Hz, 1H), (m, 12H), 1.42 (d, J = 7.2 Hz, 6H); 13 C NMR (75 MHz, CDCl 3) δ 182.3, 177.2, 176.8, 48.3, 45.4, 43.1, 29.7, 29.0, 25.8, 25.5, 18.4; Anal. Calcd for C 14H 24N 2O 4: C, 59.13; H, 8.51; N, Found: C, 59.29; H, 8.39; N S7
9 Methyl (2-ethylbutanoyl)-L-phenylalanyl-L-valinate (7i). White solid, 0.34 g, 90%, mp C; [α] D = 7.0 (c 1.0, CH 3OH); 1 H NMR (300 MHz, CD 3OD) δ (m, 5H), (m, 1H), (m, 1H), 3.09 (s, 3H), (m, 2H), (m, 6H), (m, 12H); 13 C NMR (75 MHz, CD 3OD) δ 177.5, 174.5, 174.0, 138.6, 130.4, 129.5, 129.4, 127.8, 59.0, 55.7, 40.6, 38.9, 32.0, 26.4, 26.0, 19.7, 19.1, 18.4; Anal. Calcd for C 21H 32N 2O 4: C, 66.99; H, 8.57; N, Found: C, 66.81; H, 8.47; N (Cyclohexanecarbonyl)-L-alanyl-L-leucine (7j). Yellow oil, 0.28 g, 88%; [α] D = 13.0 (c 1.0, CH 3OH); 1 H NMR (300 MHz, CD 3OD) δ (m, 2H), (m, 1H), (m, 10H), (m, 12H); 13 C NMR (75 MHz, CD 3OD) δ 180.1, 179.1, 176.3, 57.5, 52.3, 46.1, 44.4, 30.7, 30.4, 27.1, 26.9, 26.7, 17.8; Anal. Calcd for C 16H 28N 2O 4: C, 61.51; H, 9.03; N, Found: C, 61.71; H, 9.32; N S-(((Benzyloxy)carbonyl)-L-alanyl)-N-(3-(cyclohexanecarboxamido)propanoyl)-Lcysteine (7k). White solid, 0.42 g, 82%, mp C; [α] D = 14.0 (c 1.0, CH 3OH); 1 H NMR (300 MHz, 20 CD 3OD) δ (m, 5H), 5.08 (s, 2H), (m, 1H), 4.25 (q, J = 7.3 Hz, 1H), (m, 3H), 3.14 (dd, J = 13.8, 7.5 Hz, 1H), 2.38 (t, J = 6.6 Hz, 2H), (m, 1H), (m, 3H), 1.62 (d, J = 7.6 Hz, 1H), (m, 9H); 13 C NMR (75 MHz, CD 3OD) δ 203.3, 179.4, 173.8, 173.0, 158.4, 138.1, 129.6, 129.1, 128.8, 67.9, 58.4, 53.2, 46.4, 36.9, 36.3, 30.8, 30.7, 27.0, 26.9, 18.0; Anal. Calcd for C 24H 33N 3O 7S: C, 56.79; H, 6.55; N, Found: C, 57.07; H, 6.37; N (Cyclohexanecarbonyl)-L-phenylalanylglycylglycine (7l). White solid, 0.35 g, 90%, mp C; [α] D 20 = (c 1.0, CH 3OH); 1 H NMR (300 MHz, CD 3OD) δ (m, 5H), (m, 1H), S8
10 3.89 (d, J = 8.7 Hz, 2H), 3.68 (s, 2H), 3.13 (dd, J = 13.5, 5.1 Hz, 1H), 2.88 (dd, J = 13.2, 9.0 Hz, 1H), 2.14 (t, J = 8.7 Hz, 1H), (m, 4H), (m, 6H); 13 C NMR (75 MHz, CD 3OD) δ 179.4, 174.4, 172.7, 171.5, 138.4, 130.3, 129.4, 127.7, 56.3, 45.9, 43.4, 41.8, 38.4, 30.8, 30.2, 26.9, 26.8, 26.6; HRMS (ESI) C 20H 26N 3O 5 calcd.: [(M-H) - ] = found: [(M-H) - ] = S9
11 References for the Supporting Information: [1] A. R. Katritzky, Z. Wang, M. Wang, C. D. Hall, K. Suzuki, J. Org. Chem., 2005, 70, [2] L. Huizhen, G. Laurenczy, N. Yan, P. J. Dyson, Chem. Commun., 2014, 50, [3] J. E. Wilson, G. C. Fu, Angew. Chem., 2004, 116, [4] T. K. Houlding, K. Tchabanenko, Md. T. Rahman, E. V. Rebrov, Org. Biomol. Chem., 2013, 11, [5] Y. Kawagoe, K. Moriyama, H. Togo, Tetrahedron, 2013, 69, [6] H. Bo, M. A. Crider, J. P. Stables, Eur. J. Med. Chem., 2001, 36, [7] A. N. Niyazov, B. Namatov, Kh. Atlyev, Izvestiya Akademii Nauk Turkmenskoi SSR, 1974, 4, [8] Ger. Pat. DE , [9] J. M. Pochan, H. W. Gibson, J. Phys. Chem., 1974, 78, [10] S. Kim, S. Kim, N. Otsuka, I. Ryu, Angew. Chem. Int. Ed., 2005, 44, [11] A. Leone-Bay, N. Santiago, D. Achan, K. Chaudhary, F. DeMorin, L. Falzarano, S. Haas, S. Kalbag, D. Kaplan, H. Leipold, C. Lercara, D. O Toole, T. Rivera, C. Rosado, D. Sarubbi, E. Vuocolo, N. Wang, S. Milstein, R. A. Baughman, J. Med. Chem., 1995, 38, [12] R. Granger, J. Giroux, J. Lanet, M. Corbier, Bull. Soc. Chim. Fr., 1958, S10
12 1 H and 13 C Spectra of Decarboxylated Benzotriazolyl Intermediates 3a,b 1 H spectrum of 3a 13 C spectrum of 3a S11
13 1 H spectrum of 3b 13 C spectrum of 3b S12
14 1 H and 13 C Spectra of Acylated N-, O-, S-Nucleophiles 5a-k 1 H spectrum of 5a 13 C spectrum of 5a S13
15 1 H spectrum of 5b 13 C spectrum of 5b S14
16 1 H spectrum of 5c 13 C spectrum of 5c S15
17 1 H spectrum of 5d 13 C spectrum of 5d S16
18 1 H spectrum of 5e 13 C spectrum of 5e S17
19 1 H spectrum of 5f 13 C spectrum of 5f S18
20 1 H spectrum of 5g 13 C spectrum of 5g S19
21 1 H spectrum of 5h 13 C spectrum of 5h S20
22 1 H spectrum of 5i 13 C spectrum of 5i S21
23 1 H spectrum of 5j 13 C spectrum of 5j S22
24 1 H spectrum of 5k 13 C spectrum of 5k S23
25 1 H and 13 C Spectra of Acylated Amino Acids and Esters 7a g 1 H spectrum of 7a 13 C spectrum of 7a S24
26 1 H spectrum of 7b 13 C spectrum of 7b S25
27 1 H spectrum of 7c 13 C spectrum of 7c S26
28 1 H spectrum of 7d 13 C spectrum of 7d S27
29 1 H spectrum of 7e 13 C spectrum of 7e S28
30 1 H spectrum of 7f 13 C spectrum of 7f S29
31 1 H spectrum of 7g 13 C spectrum of 7g S30
32 1 H and 13 C Spectra of Acylated Di- and Tripeptides 7h l 1 H spectrum of 7h 13 C spectrum of 7h S31
33 1 H spectrum of 7i 13 C spectrum of 7i S32
34 1 H spectrum of 7j 13 C spectrum of 7j S33
35 1 H spectrum of 7k 13 Cspectra 13 C spectrum of 3a of 7k S34
36 1 H spectrum of 7l 13 C spectrum of 7l S35
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