Efficient Synthesis of Ureas by Direct Palladium-Catalyzed. Oxidative Carbonylation of Amines
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- ÍΘεριστής Βουρδουμπάς
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1 S1 Supporting Information for Efficient Synthesis of Ureas by Direct Palladium-Catalyzed Oxidative Carbonylation of Amines Bartolo Gabriele,*, Giuseppe Salerno, Raffaella Mancuso, and Mirco Costa Dipartimento di Scienze Farmaceutiche, Università della Calabria, Arcavacata di Rende, Cosenza, Italy Dipartimento di Chimica, Università della Calabria, Arcavacata di Rende, Cosenza, Italy Dipartimento di Chimica Organica e Industriale, Università di Parma, Parma, Italy Table of Contents Page S2 General Experimental Methods Pages S3 S11 Characterization of Products
2 S2 General Experimental Methods Melting points are uncorrected. 1 H NMR and 13 C NMR spectra were recorded at 300 MHz and 75 MHz, respectively, with Me 4 Si as internal standard. Chemical shifts and coupling constants (J) are given in ppm (δ) and in Hz, respectively. IR spectra were taken on a FT-IR spectrometer. Mass spectra were obtained at 70 ev on a GC-MS apparatus. Microanalyses were performed at our analytical laboratory.
3 S3 Characterization of products 1,3-Dibutylurea 2a. Colorless solid, mp C (lit C). IR (KBr) 3330 (s), 2959 (w), 2934 (w), 2871 (w), 1621 (s), 1578 (s), 1460 (w), 1233 (w) cm -1 ; 1 H NMR (CDCl 3 ) δ 5.78 (t, br, J = 5.1, 2 H, 2 NH), (m, 4 H, 2 NHCH 2 ), (m, 8 H, 2 CH 2 CH 2 CH 3 ), 0.91 (t, J = 7.3, 6 H, 2 Me); 13 C NMR (CDCl 3 ) δ 159.5, 40.0, 32.6, 20.2, 13.9; MS m/z 172 (M +, 100), 157 (17), 143 (17), 130 (39), 129 (33), 101 (45), 100 (33), 87 (31), 74 (69), 73 (27), 72 (33), 58 (16), 57 (67), 56 (33), 55 (17). Anal. Calcd for C 9 H 20 N 2 O: C, 62.75; H, 11.70, N, Found C, 62.81; H, 11.68, N, ,3-Dibenzylurea 2b. Colorless solid, mp C (lit C). IR (KBr) 3320 (m), 1627 (s), 1571 (s), 697 (m) cm -1 ; 1 H NMR (DMSO-d 6 ) δ (m, 10 H on phenyl rings), 6.48 (t, J = 5.9, 2 H, 2 NH), 4.24 (d, J = 5.9, 4 H, 2 CH 2 ); 13 C NMR (DMSO-d 6 ) δ 158.1, 140.8, 128.1, 126.9, 126.5, 42.9; MS m/z 240 (M +, 27), 149 (16), 106 (100), 91 (43), 79 (15). Anal. Calcd for C 15 H 16 N 2 O: C, 74.97; H, 6.71, N, Found C, 75.11; H, 6.72, N, ,3-Di-tert-butylurea 2c. Whitish solid, mp C (lit ). IR (KBr) 3355 (m), 2964 (m), 1637 (s), 1560 (s) cm -1 ; 1 H NMR (DMSO-d 6 ) δ 5.45 (s, 2 H, 2 NH), 1.19 (s, 18 H, 2 t-bu); 13 C NMR (DMSO-d 6 ) δ 157.0, 48.7, 29.3; MS m/z 172 (M +, 3), 157 (13), 71 (3), 61 (7), 59 (4), 58 (100), 57 (13), 56 (3). Anal. Calcd for C 9 H 20 N 2 O: C, 62.75; H, 11.70, N, Found C, 62.64; H, 11.72, N, Nomura, R.; Hasegawa, Y.; Ishimoto, M.; Toyosaki, T.; Matsuda, H. J. Org. Chem. 1992, 57, Franz, R. A.; Applegath, F.; Morriss, F. V.; Baiocchi, F. J. Org. Chem. 1961, 26,
4 S4 1,3-Diphenylurea 2d. Colorless solid, mp C (lit C). IR (KBr) 1649 (s), 1595 (m), 1559 (s), 1448 (w), 1315 (w), 1234 (m), 754 (m), 698 (m) cm -1 ; 1 H NMR (DMSO-d 6 ) δ 8.69 (s, 2 H, 2 NH), (m, 4 H on phenyl rings), (m, 4 H on phenyl rings), (m, 2 H on phenyl rings); 13 C NMR (DMSO-d 6 ) δ 152.5, 139.7, 128.7, 121.7, 118.1; MS m/z 212 (M +, 18), 119 (12), 94 (7), 93 (100), 92 (9), 91 (7), 77 (10), 66 (11), 65 (12). Anal. Calcd for C 13 H 12 N 2 O: C, 73.56; H, 5.70, N, Found C, 73.44; H, 5.71, N, ,3-Bis-(4-chlorophenyl)urea 2e. Pale yellow solid, mp C (lit ). IR (KBr) 3296 (m), 1633 (s), 1591 (s), 1557 (s), 1492 (s), 1397 (w), 1299 (w), 1237 (m), 1085 (m), 1013 (w), 823 (m), 639 (s), 507 (m) cm -1 ; 1 H NMR (DMSO-d 6 ) δ 8.88 (s, 2 H, 2 NH), (m, 4 H on phenyl rings), (m, 4 H on phenyl rings); 13 C NMR (DMSO-d 6 ) δ 152.3, 138.5, 128.6, 125.5, 119.8; MS m/z 282 (M + + 2, 8), 280 (M +, 11), 153 (13), 129 (32), 127 (100), 92 (8), 90 (7), 75 (5), 65 (10). Anal. Calcd for C 13 H 10 Cl 2 N 2 O: C, 55.54; H, 3.59; Cl, 25.22; N, Found C, 55.63; H, 3.60; Cl, 25.20; N, ,3-Bis-(4-isopropylphenyl)urea 2f. Colorless solid, mp C (lit ). IR (KBr) 3311 (m), 2959 (m), 1651 (s), 1597 (m), 1555 (s), 1514 (m), 1417 (w), 1309 (m), 1285 (w), 1236 (m), 832 (m) cm -1 ; 1 H NMR (DMSO-d 6 ) δ 8.54 (s, 2 H, 2 NH), (m, 4 H on phenyl rings), (m, 4 H on phenyl rings), 2.82 (heptuplet, J = 6.8, 2 H, 2 CHMe 2 ), 1.18 (d, J = 6.8, 12 H, 4 Me); 13 C NMR (DMSO-d 6 ) δ 152.6, 141.6, 137.4, 126.4, 118.2, 32.7, 24.0; MS m/z 296 (M +, 23), 161 (4), 146 (12), 135 (34), 133 (9), 120 (100), 103 (4), 91 (7), 77 (5). Anal. Calcd for C 19 H 24 N 2 O: C, 76.99; H, 8.16, N, Found C, 76.85; H, 8.18, N, Izdebski, J.; Pawlak, D. Synthesis 1989, Miller, R. E. J. Org. Chem. 1961, 26, Beaver, D. J.; Roman, D. P.; Stoffel, P. J. J. Org. Chem. 1959, 24, Atanassova, I. A.; Petrov, J. S.; Mollov, N. M. Synthesis 1987;
5 S5 1,3-Bis-(4-methoxyphenyl)urea 2g. Whitish solid, mp C (lit C). IR (KBr) 3302 (m), 1634 (s), 1607 (m), 1560 (s), 1511 (s), 1245 (s), 1170 (w), 1030 (w), 827 (m) cm -1 ; 1 H NMR (DMSO-d 6 ) δ 8.40 (s, 2 H, 2 NH), (m, 4 H on phenyl rings), (m, 4 H on phenyl rings), 3.71 (s, 6 H, 2 OMe); 13 C NMR (DMSO-d 6 ) δ 154.3, 153.0, 132.9, 119.9, 113.9, 55.1; MS m/z 272 (M +, 44), 149 (19), 134 (11), 123 (100), 108 (91), 95 (6), 80 (12). Anal. Calcd for C 15 H 16 N 2 O 3 : C, 66.16; H, 5.92, N, Found C, 66.28; H, 5.91, N, ,3-Dihydrobenzoimidazol-2-one 2h. Pale pink solid, mp C (lit C). IR (KBr) 3133 (m), 3027 (m), 2909 (m), 2809 (m), 1746 (s), 1485 (m), 737 (m), 705 (w), 599 (w) cm -1 ; 1 H NMR (DMSO-d 6 ) δ (s, 2 H, 2 NH), (m, 4 H aromatic); 13 C NMR (DMSO-d 6 ) δ 155.5, 129.8, 120.6, 108.7; MS m/z 134 (M +, 100), 106 (21), 105 (13), 79 (16), 67 (8), 52 (14). Anal. Calcd for C 7 H 6 N 2 O: C, 62.68; H, 4.51, N, Found C, 62.81; H, 4.50, N, H,3H-Perimidin-2-one 2i. Pale pink solid, mp C (lit C). IR (KBr) 3231 (m), 1735 (s), 1669 (w), 1647 (w), 1617 (w), 1383 (m), 815 (w), 773 (w), 755 (w) cm -1 ; 1 H NMR (DMSO-d 6 ) δ (s, 2 H, 2 NH), 7.25 (dd, J = 8.3, 7.3, 2 H aromatic), 7.14 (d, J = 8.3, 2 H aromatic), 6.60 (d, J = 7.3, 2 H aromatic); 13 C NMR (DMSO-d 6 ) δ 150.2, 137.7, 134.2, 128.0, 117.7, 113.8, 104.1; MS m/z 184 (M +, 100), 166 (60), 155 (9), 139 (9), 92 (10), 83 (9). Anal. Calcd for C 11 H 8 N 2 O: C, 71.73; H, 4.38, N, Found C, 71.64; H, 4.39, N, Tributylurea 4aa. Pale yellow oil. IR (neat) 3344 (m, br), 2956 (m), 2929 (m), 2871 (m), 1625 (s), 1537 (s), 1464 (w), 1375 (w), 1292 (w), 1236 (w), 1111 (w) cm -1 ; 1 H NMR (CDCl 3 ) δ 4.40 (t, J = 5.4, 1 H, NH), (m, 6 H, CH 2 NH + CH 2 NCH 2 ), (m, 6 H, 3 CH 2 ), 1.33 (heptuplet, J = 7.3, 6 H, 3 CH 2 ), 0.93 (t, J 7 Etter, M. C.; Urbanczyk-Lipkowska, Z.; Zia-Ebrahimi, M.; Panunto, T. W. J. Am. Chem. Soc. 1990, 112, Cairns, T. L.; Coffman, D. D.; Gilbert, W. W. J. Am. Chem. Soc. 1957, 79,
6 S6 = 7.3, 6 H, N(CH 2 CH 2 CH 2 CH 3 ) 2 ], 0.92 (t, J = 7.3, NHCH 2 CH 2 CH 2 CH 3 ); 13 C NMR (CDCl 3 ) δ 157.8, 47.1, 40.6, 32.6, 30.9, 20.26, 20.22, 13.93, 13.87; MS m/z 228 (M +, 11), 185 (11), 156 (4), 129 (4), 100 (8), 87 (7), 86 (100), 57 (14), 56 (4). Anal. Calcd for C 13 H 28 N 2 O: C, 68.37; H, 12.36, N, Found C, 68.45; H, 12.34, N, Morpholine-4-carboxylic acid butylamide 4ab. Colorless solid, mp C (lit C). IR (KBr) 3353 (m, br), 1622 (s), 1548 (s), 1405 (w), 1270 (m), 1111 (m) cm -1 ; 1 H NMR (CDCl 3 ) δ 4.99 (t, J = 5.4, 1 H, NH), (m, 4 H, CH 2 OCH 2 ), (m, 4 H, CH 2 NCH 2 ), 3.21 (td, J = 7.1, 5.4, 2 H, NHCH 2 ), (m, 2 H, NHCH 2 CH 2 ), (m, 2 H, CH 2 CH 3 ), 0.92 (t, J = 7.3, 3 H, Me); 13 C NMR (CDCl 3 ) δ 158.1, 66.6, 44.0, 40.7, 32.4, 20.1, 13.8; MS m/z 186 (M +, 14), 155 (13), 143 (8), 129 (9), 115 (5), 114 (49), 100 (7), 88 (9), 87 (50), 86 (39), 72 (9), 70 (31), 58 (8), 57 (100), 56 (33), 55 (6). Anal. Calcd for C 9 H 18 N 2 O 2 : C, 58.04; H, 9.74, N, Found C, 58.22; H, 9.72, N, Benzyl-3-butyl-1-methylurea 4ac. Pale yellow solid, mp C. IR (KBr) 3357 (m, br), 2956 (m), 2930 (m), 2869 (w), 1615 (s), 1538 (s), 1451 (m), 1388 (w), 1363 (w), 1301 (m), 1236 (m), 1175 (w), 1024 (w), 943 (w), 725 (s), 695 (m), 591 (m) cm -1 ; 1 H NMR (CDCl 3 ) δ (m, 5 H, Ph), 4.63 (t, J = 5.4, 1 H, NH), 4.48 (s, 2 H, CH 2 Ph), 3.23 (td, J = 7.3, 5.4, 2 H, HNCH 2 ), 2.85 (s, 3 H, NCH 3 ), (m, 2 H, CH 2 CH 2 CH 3 ), (m, 2 H, CH 2 CH 2 CH 3 ), 0.90 (t, J = 7.3, 3 H, CH 2 CH 2 CH 3 ); 13 C NMR (CDCl 3 ) δ 158.5, 138.2, 128.6, 127.2, 52.1, 40.7, 34.3, 32.5, 20.1, 13.8; MS m/z 220 (M +, 56), 177 (5), 148 (11), 121 (8), 120 (61), 119 (12), 118 (15), 106 (21), 92 (12), 91 (100), 72 (8), 65 (10). Anal. Calcd for C 13 H 20 N 2 O: C, 70.87; H, 9.15, N, Found C, 71.02; H, 9.16, N, ,1-Dibutyl-3-tert-butylurea 4ca. Colorless solid, mp C. IR (KBr) 3378 (m), 2960 (m), 2930 (m), 1619 (s), 1533 (s), 1491 (w), 1401 (w), 1266 (w), 1213 (m) 9 Alper, H.; Lipschutz, B. H. J. Org. Chem. 1973, 38, Hackl, K. A.; Falk, H. Monatsh.Chem. 1992, 123,
7 S7 cm -1 ; 1 H NMR (acetone-d 6 ) δ 4.77 (s, br, 1 H, NH), 3.18 (t, J = 7.3, 4 H, CH 2 NCH 2 ), (m, 4 H, 2 CH 2 CH 2 CH 3 ), (m, 4 H, 2 CH 2 CH 2 CH 3 ), 1.30 (s, 9 H t- Bu), 0.91 (t, J = 7.3, 6 H, 2 CH 2 CH 2 CH 3 ); 13 C NMR (acetone-d 6 ) δ 157.4, 50.8, 47.1, 31.5, 29.7, 20.7, 14.2; MS m/z 228 (M +, 6), 185 (5), 156 (6), 100 (5), 87 (7), 86 (100), 84 (5), 58 (5), 57 (21). Anal. Calcd for C 13 H 28 N 2 O: C, 68.37; H, 12.36, N, Found C, 68.45; H, 12.34, N, ,1-Dibutyl-3-phenylurea 4da. Colorless solid, mp C (lit C). IR (KBr) 3297 (m), 2958 (m), 1636 (s), 1533 (m), 1447 (m), 1408 (w), 1319 (w), 1243 (w), 1223 (w), 754 (m), 699 (w) cm -1 ; 1 H NMR (acetone-d 6 ) δ 7.63 (s, br, 1 H, NH), (m, 2 H on phenyl ring), (m, 2 H on phenyl ring), (m, 1 H on phenyl ring), 3.36 (t, J = 7.6, 4 H, CH 2 NCH 2 ), (m, 4 H, 2 CH 2 CH 2 CH 3 ), 1.32 (sextuplet, J = 7.3, 4 H, 2 CH 2 CH 2 CH 3 ), 0.92 (t, J = 7.3, 6 H, 2 Me); 13 C NMR (acetone-d 6 ) δ 155.7, 141.7, 129.0, 122.4, 120.5, 47.4, 31.5, 20.7, 14.2; MS m/z 248 (M +, 31), 207 (6), 205 (9), 156 (36), 120 (7), 119 (32), 100 (23), 93 (16), 92 (8), 91 (14), 86 (60), 77 (12), 65 (7), 64 (8), 57 (100). Anal. Calcd for C 15 H 24 N 2 O: C, 72.54; H, 9.74, N, Found C, 72.65; H, 9.73, N, Morpholine-4-carboxylic acid phenylamide 4db. Colorless solid, mp C (lit C). IR (KBr) 3269 (m, br), 1635 (s), 1538 (m), 1450 (m), 1415 (m), 1303 (w), 1251 (s), 1115 (m), 993 (w), 874 (w), 747 (m) cm -1 ; 1 H NMR (CDCl 3 ) δ (m, 2 H on phenyl ring), (m, 2 H on phenyl ring), 7.15 (s, br, 1 H, NH), (m, 1 H on phenyl ring), (m, 4 H, CH 2 OCH 2 ), (m, 4 H, CH 2 NCH 2 ); 13 C NMR (CDCl 3 ) δ 155.6, 139.0, 128.7, 123.3, 120.7, 66.4, 44.2; MS m/z 206 (M +, 86), 205 (9), 120 (17), 119 (51), 115 (14), 114 (100), 93 (26), 92 (14), 91 (22), 87 (23), 86 (23), 77 (28), 70 (98), 65 (16), 64 (13), 57 (49), 56 (28). Anal. Calcd for C 11 H 14 N 2 O 2 : C, 64.06; H, 6.84, N, Found C, 64.12; H, 6.82, N, Yang, Y.; Lu, S. Tetrahedron Lett. 1999, 40,
8 S8 Morpholine-4-carboxylic acid (4-methoxyphenyl)amide 4gb. Colorless solid, mp C (lit C). IR (KBr) 3266 (m), 2961 (w), 1636 (s), 1540 (m), 1516 (s), 1421 (w), 1401 (w), 1297 (m), 1234 (s), 1109 (m), 1043 (w), 841 (w), 803 (m) cm -1 ; 1 H NMR (CDCl 3 ) δ (m, 2 H on phenyl ring), 6.99 (s, br, 1 H, NH), (m, 2 H on phenyl ring), 3.75 (s, 3 H, OMe), (m, 4 H, CH 2 OCH 2 ), (m, 4 H, CH 2 NCH 2 ); 13 C NMR (CDCl 3 ) δ , , 131.9, 123.1, 113.9, 66.5, 55.4, 44.1; MS m/z 236 (M +, 70), 207 (13), 149 (100), 134 (24), 122 (16), 114 (52), 106 (11), 87 (17), 78 (10), 70 (72), 57 (27), 56 (12). Anal. Calcd for C 12 H 16 N 2 O 3 : C, 61.00; H, 6.83, N, Found C, 61.14; H, 6.82, N, Morpholine-4-carboxylic acid (9-isopropyl-4-methyl-9H-carbazol-3-yl)amide 4jb. Colorless solid, mp C. IR (KBr) 3295 (m), 1629 (s), 1522 (s), 1490 (w), 1459 (w), 1264 (m), 1115 (m), 748 (w) cm -1 ; 1 H NMR (DMSO-d 6 ) δ 8.26 (s, 1 H, NH), 8.19 (d, J = 8.3, 1 H, H-2), 7.70 (d, J = 8.3, 1 H, H-1), (m, 2 H aromatic), (m, 2 H aromatic), 5.10 (heptuplet, J = 6.8, 1 H, CHMe 2 ), (m, 4 H, CH 2 OCH 2 ), (m, 4 H, CH 2 NCH 2 ), 2.62 (s, 3 H, Me at C-4), 1.61 [d, J = 6.8, 6 H, CH(CH 3 ) 2 ]; 13 C NMR (DMSO-d 6 ) δ 156.8, 139.3, 137.0, 129.3, 128.7, 125.6, 124.6, 123.2, 122.3, 121.0, 118.3, 110.1, 107.3, 66.0, 45.8, 44.2, 20.3, 15.4; MS m/z 351 (M +, absent), 265 (14), 264 (69), 250 (20), 249 (100), 222 (17), 221 (14), 193 (19), 192 (10), 167 (6), 166 (6). Anal. Calcd for C 21 H 25 N 3 O 2 : C, 71.77; H, 7.17, N, Found C, 71.67; H, 7.18, N, [3-(1-Methoxycarbonyl-2-phenylethyl)ureido]-3-phenylpropionic acid methyl ester 7a. Colorless solid, mp C (lit C). IR (KBr) 3356 (m), 1742 (s), 1715 (s), 1635 (s), 1577 (s), 1440 (m), 1358 (w), 1303 (m), 1213 (m), 1177 (w), 699 (m) cm -1 ; 1 H NMR (DMSO-d 6 ) δ (m, 10 H on phenyl rings),
9 S (d, J = 7.8, 2 H, 2 NH), 4.40 (td, J = 7.8, 5.4, 2 H, CHCH 2 ), 3.59 (s, 6 H, 2 CO 2 Me), 2.98 (distorted dd, J = 13.7, 5.4, 2 H, 2 CHH), 2.89 (distorted dd, J = 13.7, 7.8, 2 H, 2 CHH); 13 C NMR (DMSO-d 6 ) δ 172.6, 156.6, 136.9, 129.1, 128.2, 126.5, 53.9, 51.6, 37.4; MS m/z 384 (M +, absent), 353 (8), 352 (35), 293 (13), 292 (10), 207 (14), 190 (13), 163 (53), 162 (98), 161 (30), 131 (59), 128 (19), 120 (15), 104 (20), 103 (16), 92 (11), 91 (100), 77 (13), 65 (12). Anal. Calcd for C 21 H 24 N 2 O 5 : C, 65.61; H, 6.29, N, Found C, 65.70; H, 6.30, N, [3-(1-Methoxycarbonylethyl)ureido]propionic acid methyl ester 7b. Colorless solid, mp C (lit C). IR (KBr) 3342 (s), 1750 (s), 1737 (s), 1629 (s), 1585 (s), 1451 (w), 1435 (w), 1355 (w), 1335 (w), 1224 (s), 1153 (s), 641 (m) cm -1 ; 1 H NMR (DMSO-d 6 ) δ 6.43 (d, J = 7.3, 2 H, 2 NH), 4.15 (quintuplet, J = 7.3, 2 H, 2 CH), 3.62 (s, 6 H, 2 CO 2 Me), 1.24 (d, J = 7.3, 6 H, 2 CHCH 3 ); 13 C NMR (DMSO-d 6 ) δ 174.1, 156.7, 51.7, 48.1, 17.9; MS m/z 232 (M +, absent), 200 (6), 142 (8), 141 (100), 113 (36), 70 (29). Anal. Calcd for C 9 H 16 N 2 O 5 : C, 44.55; H, 6.94, N, Found C, 44.61; H, 6.92, N, [3-(1-Methoxycarbonyl-3-methylbutyl)ureido]-4-methylpentanoic acid methyl ester 7c. Colorless solid, mp C (lit C). IR (KBr) 3360 (m), 2961 (m), 1755 (s), 1749 (s), 1643 (s), 1574 (s), 1437 (w), 1375 (w), 1248 (w), 1199 (m), 1171 (m) cm -1 ; 1 H NMR (DMSO-d 6 ) δ 6.34 (d, J = 8.3, 2 H, 2 NH), (multiplet, 2 H, 2 NHCHCH 2 ), 3.61 (s, 6 H, 2 CO 2 Me), (m, 2 H, CHMe 2 ), 1.45 (t, J = 7.3, CHCH 2 CH), 0.90 (d, J = 6.8, 6 H, 2 CHCH 3 ), 0.86 (d, J = 6.8, 2 CHCH 3 ); 13 C NMR (DMSO-d 6 ) δ 173.9, 157.1, 51.6, 50.9, 40.9, 24.2, 22.7, 21.5; MS m/z 316 (M +, absent), 228 (28), 225 (47), 209 (15), 157 (100), 155 (12), 141 (12), 129 (13), 100 (21), 86 (27), 70 (18), 69 (20), 55 (17). Anal. Calcd for C 15 H 28 N 2 O 5 : C, 56.94; H, 8.92, N, Found C, 58.01; H, 8.90, N, Buntain, I. G.; Suckling, C. J.; Wood, H. C. S. J. Chem. Soc. Perkin Trans , Chang, Y.-G.; Lee, H.-S.; Kim, K. Tetrahedron Lett. 2001, 42,
10 S10 2-[3-(1-Methoxycarbonyl-3-methylpropyl)ureido]-3-methylbutyric acid methyl ester 7d. Colorless solid, mp C. IR (KBr) 3335 (m), 2965 (m), 1745 (s), 1633 (s), 1573 (s), 1435 (w), 1372 (w), 1309 (w), 1206 (m), 1147 (m) cm -1 ; 1 H NMR (DMSO-d 6 ) δ 6.42 (d, J = 8.8, 2 H, 2 NH), 4.08 (dd, J = 8.8, 5.4, 2 H, 2 NHCH), 3.63 (s, 6 H, 2 CO 2 Me), (m, 2 H, 2 CHMe 2 ), (t, J = 7.8, 6 H, 2 CH 3 CHCH 3 ), (t, J = 7.8, 6 H, 2 CH 3 CHCH 3 ); 13 C NMR (DMSO-d 6 ) δ 173.0, 157.5, 57.6, 51.5, 30.5, 19.0, 17.7; MS m/z 288 (M +, <0.5%), 257 (1), 229 (31), 154 (3), 130 (7), 88 (37), 73 (6), 72 (100), 55 (11). Anal. Calcd for C 13 H 24 N 2 O 5 : C, 54.15; H, 8.39, N, Found C, 54.23; H, 8.41, N, (S,S)-2-[3-(1,3-Bis-methoxycarbonylpropyl)ureido]pentanedioic acid dimethyl ester 7e. Colorless solid, mp C (lit C). IR (KBr) 3355 (m), 1746 (s), 1731 (s), 1642 (m), 1633 (s), 1573 (m), 1567 (m), 1556 (m), 1455 (m), 1435 (m), 1206 (s), 1167 (m), 982 (w), 784 (w) cm -1 ; 1 H NMR (DMSO-d 6 ) δ 5.88 (d, J = 8.3, 2 H, 2 NH), 4.53 (td, J = 8.3, 5.4, 2 H, 2 CH), 3.75 (s, 6 H, 2 CO 2 Me), 3.67 (s, 6 H, 2 CO 2 Me), (m, 4 H, 2 CH 2 CO 2 Me), (m, 2 H, 2 CHCHH), (m, 2 H, 2 CHCHH); 13 C NMR (DMSO-d 6 ) δ 173.6, 173.5, 157.1, 52.45, 52.37, 51.8, 30.1, 28.1; MS m/z 376 (M +, absent), 344 (2), 312 (43), 285 (27), 284 (38), 281 (19), 280 (19), 253 (66), 252 (46), 239 (11), 226 (18), 225 (100), 224 (31), 221 (40), 193 (67), 192 (11), 165 (16), 142 (35), 138 (17), 110 (25), 84 (52), 82 (54), 59 (15), 56 (17), 55 (17). Anal. Calcd for C 15 H 24 N 2 O 9 : C, 47.87; H, 6.43, N, Found C, 47.99; H, 6.42, N, Humphlett, W. J.; Wilson, C.V. J. Org. Chem. 1961, 26,
11 S11 (3-Methoxycarbonylmethylureido)acetic acid methyl ester 7f. Colorless solid, mp C (lit C). IR (KBr) 3351 (m), 1754 (s), 1633 (s), 1593 (s), 1437 (w), 1419 (w), 1375 (w), 1218 (m), 1200 (m), 1171 (w), 970 (w), 609 (w) cm -1 ; 1 H NMR (DMSO-d 6 ) δ 6.57 (t, J = 5.9, 2 H, 2 NH), 3.80 (d, J = 5.9, 4 H, 2 CH 2 ), 3.62 (s, 6 H, 2 CO 2 Me); 13 C NMR (DMSO-d 6 ) δ 171.5, 157.8, 51.5, 41.3; MS m/z 204 (M +, absent), 172 (10), 141 (15), 140 (55), 113 (100), 100 (17), 85 (64), 59 (9), 56 (57). Anal. Calcd for C 7 H 12 N 2 O 5 : C, 41.18; H, 5.92, N, Found C, 41.03; H, 5.91, N, [(Morpholine-4-carbonyl)amino]acetic acid methyl ester 8fb. Colorless solid, mp C. IR (KBr) 3303 (m), 1732 (s), 1621 (s), 1548 (m), 1539 (m), 1417 (w), 1351 (w), 1315 (w), 1274 (w), 1249 (m), 1115 (m), 1004 (w), 960 (w), 852 (w) cm -1 ; 1 H NMR (DMSO-d 6 ) δ 7.05 (t, J = 5.9, 1 H, NH), 3.74 (d, J = 5.9, 2 H, NHCH 2 ), 3.61 (s, 3 H, CO 2 Me), (m, 2 H, CH 2 OCH 2 ), (m, 4 H, CH 2 NHCH 2 ); 13 C NMR (DMSO-d 6 ) δ 171.5, 157.6, 65.9, 51.5, 43.8, 42.1; MS m/z 202 (M +, 19), 171 (14), 143 (22), 114 (81), 113 (14), 88 (39), 87 (54), 86 (46), 70 (46), 57 (100), 56 (84). Anal. Calcd for C 8 H 14 N 2 O 4 : C, 47.52; H, 6.98, N, Found C, 47.65; H, 7.00, N, Kondo, K.; Murata, K.; Miyoshi, N.; Murai, S.; Sonoda, N. Synthesis 1979,
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