Aqueous MW eco-friendly protocol for amino group protection.
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1 Electronic Supplementary Material (ESI) for RSC Advances. This journal is The Royal Society of Chemistry 215 Aqueous MW eco-friendly protocol for amino group protection. M. ardi, a. errera Cano, b P. Costanzo, c M. liverio, c G. Sindona a and A. Procopio c a Dipartimento di Chimica, Università della Calabria Cubo 12C, 8736-Arcavacata di Rende (CS), Italia. E- mail: monica.nardi@unical.it. Fax: ; Tel: b IFIQC, Departamento de Química rgánica, Facultad de Ciencias Químicas, Universidad acional de Córdoba, Ciudad Universitaria, Córdoba 5, Argentina. c Dipartimento di Scienze della Salute, Università Magna Graecia, Viale Europa, 88-Germaneto (CZ), Italia. General methods and experimental procedures. 2 1, 13 C and MS spectra of compounds... 7
2 General: All chemicals and solvents were purchased from common commercial sources and were used as received without any further purification. All reactions were monitored by TLC on silica Merck F254 percolated aluminum plates and were developed by spraying with ninhydrin solution when possible or with a GC-MS Shimadzu workstation, constituted by a GC 21 (provided of a 3 m- QUADREX 7 5MS capillary column, operating in splitless mode, 1 ml min 1 flow of e as carrier gas) and a 21 quadrupole mass-detector. All reactions were carried out in the a Syntos 3 Microwave oven (Anton-Paar) with rotor 4 24MG5. Proton nuclear magnetic resonance ( 1 - MR) spectra were recorded on a Brücker spectrometer at 3 Mz. Chemical shifts are reported in δ units with TMS as reference (δ.). All coupling constants (J) are reported in ertz. Multiplicity is indicated by one or more of the following: s (singlet), d (doublet), t (triplet), q (quartet), m (multiplet). Carbon nuclear magnetic resonance ( 13 C-MR) spectra were recorded on a Brücker at 3 Mz. Chemical shifts are reported in δ units relative to CDCl 3 (δ 77.). Melting points were obtained on a Kofler apparatus. General Procedure to determine the substrate scope To a stirred solution of tosyl chloride, fmoc chloride, boc anidride and acetyl chloride (2.2 mmol), in 2 (3 ml) was added the -nucleophile (2. mmol) and conducted in MW. The reaction mixture until TLC indicated consumption of the starting material. The reaction mixture presents a organic precipitate. The same, repeatedly washed with water is subsequently dried. -Benzyl-p-toluenesulfonamide (1a): yellow solid obtained in 9 % yield (mp C); 1 -MR (3 Mz, CDCl 3 ): = 7.76 (d, 2, J = 8.24, C ar ), (m, 4, C ar ), , (m, 2, C ar ), 4.76 ( t, 1,, J = 6.15), 4.11 (d, 2, C 2, J = 6.22), 2.44 (s, 3, C 3 ). 13 C-MR (75 Mz, CDCl 3 ): 21.85, 47.59, , , 128.2, 129.1, 136.7, , , (9-Fluorenylmethoxycarbonyl) benzylamine (1b): Colorless solid obtained in 98 % yield. 1 -MR (3 Mz, CDCl 3 ): = (m, 4, C ar ), (m, 5, C ar ), 4.51 (dd, 2, C 2 ), (m, 2, C 2 ). 13 C-MR (75 Mz, CDCl 3 ): 46.2, 47.32, 66.71, 79.74, 125., 127.5, , , , , , , , , (tert-butoxycarbonyl) benzylamine (1c): white solid obtained in 98% yield (mp C); 1 -MR (3 Mz, CDCl 3 ): = (m, 5, Car), 4.31 (d, J= 5.49, 2), 1.46 (s, 9) 13 C-MR (75 Mz, CDCl 3 ): 46.2, 47.32, 66.71, 79.74, 125., 127.5, , , , , , , , , benzylacetamide (1d): yellow flake solid obtained in 98% yield (mp -62 C). Spectroscopic data compared to those of the pure product.
3 -phenyl-p-toluenesulfonamide (2a): white solid obtained in 98 % yield (mp C);. 1 -MR (3 Mz, CDCl 3 ): 7.67 (d, J= 7.5 z, 2, Car), (m, 5, -Ar), 7.11 (d, J= 7.5 z, 2, Car), 2.38 (s, 3, C 3 ), 1.74, (s, 1, ). 13 C-MR (75 Mz, CDCl 3 ): 21.5, 111.1, 121.1, 125.7, 126., 129.5,136.7, (9-fluorenylmethoxycarbonyl) aniline (2b): Brown solid obtained in 92 % yield; 1 - MR (3 Mz, CDCl 3 ) 7.79 (d, 2, Car, J=7.4 z), 7.63 (d, 2, Car, J=7. z), (m, 8, Car), 6.63 (br s, 1), 4.56 (d, 2, J=6.4 z), 4.28 (t, 1, J=6.4 z). 13 C-MR (75 Mz, CDCl 3 ) : 47.1, 66.8, , 12., 123.6, 124.9, 127.1, 127.8, 129.1, 137.7, 141.4,143.8, (tert-butoxycarbonyl) aniline (2c): White solid obtained in 94 % yield (mp C); 1 -MR (3 Mz, CDCl 3 ) 1 -MR (3 Mz, CDCl 3 ): ( m, 4 ), 1.52 (s, 9), 7.25 (tt, 1, Ar, J= 7.27; J= 1.38), 6.49 (s, 1, ), 13 C-MR (75 Mz, CDCl 3 ): 28.69, 8.83, , , , , Acetyl aniline (2d): White solid obtained in 98 % yield ( C). Spectroscopic data compared to those of the pure product. -toluidine p-toluenesulfonamide (3a): Coloress oil obtained in 98 % yield. Spectroscopic data compared to those of the pure product. -(9-Fluorenylmethoxycarbonyl)-toluidine (3b): colorless solid obtained in 9 % yield (mp ºC). 1 -MR (3 Mz, CDCl 3 ) δ= (m, 2, C ar ), (m, 2, C ar ), (m, 6, C ar ), (m, 2, C ar ), (m, 4, C ar ), 4.53 (m, 2), 4.27 (br, 1, ), 2.3 (s, 3), 13 C-MR (75 Mz, CDCl 3 ) δ = 2.76, 47.17, 66.74, 12.3, , , , , (tert-butoxycarbonyl)-toluidine (3c): brow solid obtained in 98 % yield (mp ºC); 1 -MR (3 Mz, CDCl 3 ): = (m, 2, C ar ), 7.8 (d, J= 8.25, 2, C ar ), 6.56 (s, 1, ), 2.29 (s, 3), 1.5 (s, 9); 13 C-MR (75 Mz, CDCl 3 ): 28.69, 8.64, 119.3, , , 136.6, Acetyl-toluidine (3d): off white to brown flake solid obtained in 97 % yield (mp ºC). -(p-nitro-aniline) p-toluenesulfonamide (4a): yellow flake solid obtained in 85 % yield (mp C). Spectroscopic data compared to those of the pure product. -(9-fluorenylmethoxycarbonyl) p-nitro-aniline (4b): yellow solid obtained in 8 % yield. C; 1 -MR (3 Mz, CDCl 3 ): = (m, 2, Car), (m, 1, Car), (m, 1, C), 4.26 (t, 2, C 2, J = 6.5). 13 C-MR (75 Mz, CDCl 3 ): 46.2, 47.32, 66.71, 79.74, 125., 127.5, , , , , ,
4 141.33, , , ( tert-butoxycarbonyl) p-nitro-aniline (4c) yellow flake oil obtained in 98 % yield. Spectroscopic data compared to those of the pure product. -p-nitro-aniline acetamide (4d): Solid, yellow obtained in 96% yield (mp C). Spectroscopic data compared to those of the pure product. -p-nitro-aniline-p-toluenesulfonamide (5a) white solid obtained in 98% yield (mp C). Spectroscopic data compared to those reported in the literature. 2 -(9-fluorenylmethoxycarbonyl) p-methoxybenzylamine (5b): yellow solid obtained in 95 % yield (mp ). 1 MR (3 Mz, CDCl 3 ) : 7.77 (d, 2, J=7. z), 7.59 (d, 2, J=5.8 z), (m, 6), 6.87 (d, 2, J=6.9 z), 4.45 (d, 2, J=5.5 z), (m, 5 ) 3.8 (s, 3). 13 C-MR (75 Mz, CDCl 3 ) : 44.6, 47.3, 55.3, 66.6, 114.1, 12., 125., 127., 127.7, 128.9, 13.5, 141.3, 143.9, 156.3, (tert-butoxycarbonyl) p-methoxybenzylamine (5c): colourless oil MR (3 Mz, CDCl 3 ) = (m, 2, Car), (m, 2, Car), (m, 2, C 2 ), 3.79 (s, 3), 1.47 (s, 9), 13 C-MR (75 Mz, CDCl 3 ): 28.76, 44.52, 55.64, 79.74, , , , , p-methoxybenzyl acetamide (5d): yellow oil obtained in 97 % yield. Spectroscopic data compared to those of the pure product. -ctyl p-toluenesulfonamide (6a): yellow oil obtained in 83 % yield. 1 -MR (3 Mz, CDCl 3 ) = 7.73 (d, J= 7.4 z, 2, Car), 7.31 (d, J= 7.4 z, 2, Car), (m, 2, C 2 ), 2.4 (s, 3, C 3 ), (m, 2, C 2 ), (m, 1, 5 C 2 ),.9-1. (m, 3, C 3 ),. 13 C-MR (75 Mz, CDCl 3 ): 14.38, 22.83, 24.53, 43.53, 27.11, 29.48, 29.61, 31.23, 41.5, , , , (9-fluorenylmethoxycarbonyl) ctylamine (6b): Pale yellow solid obtained in 95% yield (mp 91-93ºC). 1 -MR (3 Mz, CDCl 3 ): = (m, 8, C ar ), (m, 2, C 2 ), (m, 1, C), 3.19 (dd, 2, C 2, J = 12.9, J = 6.66), (m, 2, C 2 ), (m, 1, 5 C 2 ),.9-.7 (m, 3, C 3 ). 13 C-MR (75 Mz, CDCl 3 ): 14.42, 22.97, 44.52, 27.7, 29.54, 29.57, 32.12, 41.44, 47.65, 66.8, 12.28, , , , , , (tert-butoxycarbonyl) ctylamine (6c): Colourless oil obtained in 91% yield. Spectroscopic data compared to those reported in the literature. 21 -ctyl acetamide (6d): Colorless oil obtained in 97% yield. Spectroscopic data compared to those of the pure product.
5 p-toluenesulfonamide phenylalanine (7a): White solid obtained in 98 % yield (mp C). Spectroscopic data compared to those of the pure product. -(9-fluorenylmethoxycarbonyl)-phenylalanine (7b): white solid obtained in 92 % yield (mp C). Spectroscopic data compared to those of the pure product. -(tert-butoxycarbonyl)-phenylalanine (7c): white solid obtained in 94 % yield (mp C). Spectroscopic data compared to those of the pure product. -Acetil-phenylalanine (7d): white solid obtained in 97 % yield (mp C). Spectroscopic data compared to those of the pure product. p-toluenesulfonamide phenylalanine methyl ester (8a): white solid obtained in 94% yield. 1 -MR (CDCl 3, 3 Mz) 7.63 (d, J=8.25 z, 2), (M, 5), 7.5 (dd, J=5.42, 2.2 z, 2), 5.8 (d, 1,, J = 9.6), 4.2 (dt, J= 9.6, J = 5.9, z, 2), 3.48 (s, 3, C 3 ), 3.2 (d, 2, J = 5.9), 2.4 (s, 3, C 3 ); 13 C-MR (CDCl 3, 75 Mz) 21.84, 39.7, 52.68, 56.93, 127.5, , 128.9, , , , , , (9-fluorenylmethoxycarbonyl)-phenylalanine methyl ester (8b): white solid obtained in 92% yield. 1 -MR (CDCl 3, 3 Mz) d 7.76 (d, J=7.5 z, 2), 7.56 (t, J=6.7 z, 2), 7.4 (td, J=7.5,.6 z, 2), (m, 5), 7.8 (d, J=6.5 z, 2), 5.26 (d, J=8.1 z, 1), 4.67 (m, 1), 4.44 (dd, J=1.6, 7.1 z, 1), 4.34 (dd, J=1.6, 6.9 z, 1), 4.2 (t, J=7. z, 1), 3.73 (s, 3), 3.11 (m, 2); 13 C-MR (CDCl 3, 75 Mz) 38.4, 47.3, 52.6, 54.9, 67.1, 12.2, 125.3, 127.3, 127.4, 127.9, 128.8, 129.5, 135.9, 141.5, 144., 155.7, (tert-butoxycarbonyl)-phenylalanine methyl ester (8 c): white solid obtained in 96% yield. (mp 36-4 C). Spectroscopic data compared to those of the pure product. -Acetil-phenylalanine methyl esther (8d): colorless oil obtained in 95% yield. Spectroscopic data compared to those of the pure product. p-toluenesulfonamide alanine (9a): white solid obtained in 96% (mp C). Spectroscopic data compared to those of the pure product. -(9-fluorenylmethoxycarbonyl)-alanine (9b): white solid obtained in 96% (mp C). Spectroscopic data compared to those of the pure product. -(tert-butoxycarbonyl)- alanine (9c): white solid obtained in 96% (mp C). Spectroscopic data compared to those of the pure product. -Acetil-alanine (9d): white solid obtained in 96 % yield. (mp C). Spectroscopic data compared to those of the pure product.
6 p-toluenesulfonamide alanine methyl ester (1a): white solid obtained in 98% yield (mp C). Spectroscopic data compared to those reported in the literature. 22 -(9-fluorenylmethoxycarbonyl)-alanine methyl ester (1b): white solid obtained in 92% yield (mp C). Spectroscopic data compared to those of the pure product. -(tert-butoxycarbonyl)-alanine methyl ester (1c): colorless oil obtained in 93% yield. Spectroscopic data compared to those reported in the literature. 23 -Acetil-alanine methyl ester (1 d): colorless oil obtained in 97% yield. Spectroscopic data compared to those of the pure product. p-toluenesulfonamide isoleucine (11a): white solid obtained in 86% yield (mp C). Spectroscopic data compared to those of the pure product. -(9-fluorenylmethoxycarbonyl)-isoleucine (11b): white solid obtained in 8% yield (mp C). Spectroscopic data compared to those of the pure product. -(tert-butoxycarbonyl)-isoleucine (11c) white solid obtained in 85% yield (mp C). Spectroscopic data compared to those of the pure product. -Acetil-isoleucine (11d) white solid obtained in 87% yield (mp C). Spectroscopic data compared to those of the pure product. p-toluenesulfonamide isoleucine methyl ester (12a): white solid obtained in 98% yield (mp C). Spectroscopic data compared to those reported in the literature. 24 -(9-fluorenylmethoxycarbonyl) isoleucine methyl ester (12b): white solid obtained in 93% yield (mp C). Spectroscopic data compared to those of the pure product. -(tert-butoxycarbonyl)-isoleucine methyl ester (12c): white solid obtained in 97% yield (mp 68-72ºC). Spectroscopic data compared to those of the pure product. -Acetil-isoleucine methyl ester (12d): colorless oil obtained in 95% yield. Spectroscopic data compared to those of the pure product.
7 1, and 13 C spectra of compounds 1a S AME : nat36 EXP : 1 PRC : 1 Integral / / AME : nat36c13 EXP : 1 PRC :
8 1b AME : nat57 EXP : 1 PRC : 1 Integral AME : nat57c13 EXP : 1 PRC :
9 1c AME : nat44 EXP : 1 PRC : 1 /2 Integral AME : nat44c13 EXP : 1 PRC :
10 2b AME : nat58c13 EXP : 1 PRC :
11 2c AME : nat29 EXP : 1 PRC : 1 /2 Integral AME : nat29c13 EXP : 1 PRC :
12 3b AME : nat28 EXP : 2 PRC : 1 Integral / AME : nat28c13 EXP : 1 PRC :
13 3c AME : : EXP : WISPC1D PRC : AT3 /4 Integral AME : nat3c13 EXP : 3 PRC :
14 4b 2 AME : nat55c13 EXP : 1 PRC :
15 5c 3 C AME : nat31 EXP : 1 PRC : 1 /4 Integral AME : nat31c13 EXP : 1 PRC :
16 6b
17 6c AME : nat45 EXP : 1 PRC : 1 /2 Integral AME : nat45c13 EXP : 2 PRC :
18 C 3 S 8a AME : nat38 EXP : 1 PRC : 1 Integral AME : nat38c13 EXP : 1 PRC :
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