Molecules 2016, 21, 815
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172.58, 81.88, 71.50, 60.49, 60.39, 43.92, 38.10, 34.56. MS (ES+) m/z (%) = 156 [MH+] (46), 88 (13), 68 (100)
.
Ethyl 3-(4,5-dihydro-1,3-thiazol-2-ylamino)propanoate (3g) [31]. Yellow oil. IR (neat, cm´1):
ν
= 3395, 3051,
2955, 2858, 1728, 1651, 1612, 1558, 1504, 1447, 1416, 1373, 1354, 1308, 1277, 1238, 1169, 1115, 1042, 984,
1
941, 918, 928, 733, 698. H-NMR (CDCl3, 500 MHz):
δ (ppm) 4.10 (q, J = 8.1 Hz, 2H), 3.75–3.61 (m, 2H),
3.61–3.45 (m, 2H). 3.22–3.14 (m, 2H), 2.71–2.59 (m, 2H), 1.24 (t, J = 8.3 Hz, 3H).
Ethyl 3-(phenylamino)propanoate (3h) [32]. Orange oil. IR (neat, cm´1):
= 3401, 3053, 3022, 2980, 2933,
2904, 2870, 1736, 1720, 1604, 1558, 1506, 1375, 1317, 1251, 1180, 1114, 1099, 1047, 1028, 869, 858, 750, 692.
1H-NMR (CDCl3, 500 MHz):
(ppm) 7.18 (t, J = 7.4 Hz, 2H), 6.72 (t, J = 6.4 Hz, 1H), 6.62 (d, J = 8.7 Hz,
ν
δ
2H), 4.14 (q, J = 7.2 Hz, 2H), 4.02 (broad s, 1H), 3.45 (t, J = 6.4 Hz, 2H), 2.61 (t, J = 6.4 Hz, 2H), 1.26 (t,
J = 7.2 Hz, 3H).
Ethyl 3-(benzylamino)propanoate (3i) [30]. Yellow oil. IR (neat, cm´1):
2904, 2835, 1732, 1496, 1454, 1373, 1350, 1180, 1119, 1095, 1029, 737, 698. H-NMR (CDCl3, 500 MHz):
ν = 3325, 3086, 3062, 3028, 2981,
1
δ
(ppm) 7.31 (d, J = 4.7 Hz, 4H), 7.28–7.19 (m, 1H), 4.14 (q, J = 7.1 Hz, 2H), 3.80 (s, 2H), 2.90 (t, J = 6.5 Hz,
2H), 2.53 (t, J = 6.5 Hz, 2H), 1.25 (t, J = 7.2 Hz, 3H).
Ethyl 3-(4-ethylphenylamino)propanoate (3j) [33]. Dark-brown oil. IR (neat, cm´1):
2932, 2870, 1732, 1616, 1520, 1473, 1458, 1396, 1373, 1315, 1242, 1180, 1126, 1095, 1045, 1026, 822.
1H-NMR (CDCl3, 500 MHz):
(ppm) 7.00 (d, J = 8.5 Hz, 2H), 6.56 (d, J = 8.5 Hz, 2H), 4.14 (q, J = 7.1 Hz,
2H), 3.89 (broad s, 1H), 3.42 (t, J = 6.4 Hz, 2H), 2.59 (t, J = 6.4 Hz, 2H), 2.52 (q, J = 7.6 Hz, 2H), 1.25 (t,
ν = 3395, 3101 2963,
δ
J = 7.2 Hz, 3H), 1.17 (t, J = 7.6 Hz, 3H). 13C-NMR (CDCl3, 126 MHz):
δ (ppm) 172.47, 145.58, 133.64,
128.63, 113.28, 60.59, 39.83, 34.04, 27.93, 15.95, 14.21. MS (ES+) m/z (%) = 222 [MH+] (10), 134 (100),
119 (1).
Ethyl 3-(4-methoxyphenylamino)propanoate (3k) [34]. Dark-brown oil. IR (neat, cm´1):
3067, 2986, 2955, 2940, 2909, 2835, 1724, 1627, 1513, 1465, 1458, 1442, 1373, 1296, 1238, 1180, 1119,
1092, 1034, 826, 760, 725. 1H-NMR (CDCl3, 500 MHz):
(ppm) 6.77 (d, J = 9.0 Hz, 2H), 6.60 (d,
ν = 3383, 3237,
δ
J = 9.0 Hz, 2H), 4.14 (q, J = 7.1 Hz, 2H) 3.73 (s, 3H), 3.39 (t, J = 6.4 Hz, 2H), 2.58 (t, J = 6.4 Hz, 2H), 1.25 (t,
J = 7.2 Hz, 3H).
Ethyl 3-(isobutylamino)propanoate (3l) [35]. Yellow oil. IR (neat, cm´1): υ = 2964, 2927, 2875, 2247, 1454,
1377, 698. 1H-NMR (CDCl3, 250 MHz):
δ (ppm) 0.91 (t, J = 7.33 Hz, 3H), 1.05 (d, J = 6.1 Hz, 3H),
1.27–1.57 (m, 1H), 2.05 (s, 1H), 2.51 (t, J = 6.7 Hz, 1H), 2.61 (sx, J = 6.7 Hz, 1H), 2.85-3.05 (m, 1H), 3.48 (q,
J = 6.7 Hz, 1H), 4.55 (q, J = 6.7 Hz, 1H). 13C-NMR (CDCl3, 62.9 MHz):
δ (ppm) 10.1, 19.1, 19.8, 29.5,
42.5, 53.9, 118.8.
Methyl 3-(prop-2-en-1-yl)propanoate (6e) [36]. Light-yellow oil. IR (neat, cm´1):
1736, 1728, 1643, 1558, 1456, 1436, 1364, 1238, 1196, 1177, 920, 854, 790. H-NMR (CDCl3, 500 MHz):
ν = 3323, 3076, 2953,
1
δ
(ppm) 5.91–5.83 (m, 1H), 5.18 (dq, J = 17.2, 1.7 Hz, 1H), 5.10 (dq, J = 10.3, 1.6 Hz, 1H), 3.69 (s, 3H), 3.26
(dt, J = 3.0, 1.4 Hz, 2H), 2.89 (t, J = 6.5 Hz, 2H), 2.53 (t, J = 6.5 Hz, 2H). 13C-NMR (CDCl3, 126 MHz):
δ(ppm) 173.19, 136.51, 116.11, 52.19, 51.62, 44.38, 34.51.
Methyl 3-(prop-2-yn-1-ylamino)propanoate (6f). Dark-orange oil. IR (neat, cm´1):
2928, 2851, 2098, 1732, 1458, 1438, 1373, 1246, 1177, 1119, 1045, 1018, 910, 844, 756. H-NMR (CDCl3,
ν
= 3291, 2982, 2954,
1
500 MHz):
δ (ppm) 3.70 (s, 3H), 3.44 (d, J = 2.4 Hz, 2H), 2.98 (t, J = 6.5 Hz, 2H), 2.54 (t, J = 6.5 Hz, 2H),
2.22 (t, J = 2.4 Hz, 1H). 13C-NMR (CDCl3, 126 MHz):
δ (ppm) 172.56, 81.88, 71.51, 60.49, 48.99, 43.92,
38.10, 34.56, 14.21. MS (ES+) m/z (%) = 142 [MH+] (10), 75 (13), 68 (100).
Methyl 3-(4-methoxybenzylamino)propanoate (6m) [27]. Yellow oil. IR (neat, cm´1): ν = 3421, 3067, 2997,
2951, 2909, 2835, 1732, 1612, 1585, 1512, 1458, 1439, 1416, 1362, 1300, 1246, 1172, 1107, 1034, 818, 775,
1
756, 702. H-NMR (CDCl3, 500 MHz):
δ (ppm) 7.21 (d, J = 8.7 Hz, 2H), 6.80 (d, J = 8.7 Hz, 2H), 3.78 (s,
3H), 3.72 (s, 2H), 3.66 (s, 3H), 2.87 (t, J = 6.5 Hz, 2H), 2.52 (t, J = 6.5 Hz, 2H).