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was purified by column chromatography (silica gel; eluent, hexane/AcOEt = 2/1 - 1/1) to give 6b (439 mg,
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85%) as a colorless oil. H NMR (CDCl3) δ (ppm): 1.36-1.92 (4H, m, including 1.40, t, J = 5.0 Hz),
1.95-2.12(1H, m), 3.39 (3H, s), 3.60-3.72 (2H, m), 4.62 (1H, d, J = 6.8 Hz), 4.65 (1H, d, J = 6.8 Hz), 4.74
(1H, dd, J = 6.8, 7.8 Hz), 7.15-7.21 (2H, m), 7.30-7.42 (1H, m), 8.19 (1H, d, J = 8.0 Hz), 10.11 (1H, br s). IR
(neat): 3301, 2950, 1732, 1594, 1546, 1454, 1283, 1156, 1027, 908, 762, 723 cm-1. HRFAB-MS calcd for
C14H18NO4F3Li (M+Li)+: 328.1348, found: 328.1359.
N-[2-(4-Hydroxy-1-methoxymethoxybutyl)phenyl]-4-nitrobenzamide (6c)
As a yellow oil, 6c (975 mg, 89%) was obtained by the same treatment of 12 (900 mg, 2.9 mmol) with
4-nitrobenzoyl chloride (810 mg, 4.4 mmol) as the case of 6b. 1H NMR (CDCl3) δ (ppm): 1.32-1.99 (4H,
m), 2.02-2.20 (1H, m), 3.41 (3H, s), 5.54-5.73 (2H, m), 4.68 (1H, d, J = 6.8 Hz), 4.71 (1H, d, J = 6.8 Hz),
4.77 (1H, t, J = 7.3 Hz), 7.09-7.24 (2H, m), 7.33-7.45 (1H, m), 8.04-8.18 (2H, m), 8.30-8.46 (3H, m), 9.93
(1H, br s). 13C NMR (CDCl3) δ (ppm): 29.1, 31.7, 56.1, 62.1, 79.1, 94.6, 122.7, 124.0, 124.9, 128.2, 128.9,
129.0, 129.6, 136.0, 140.3, 149.6, 162.9. IR (neat): 3344, 2948, 1678, 1604, 1590, 1526, 1450, 1348, 1313,
1027, 853, 761, 714 cm-1. HRFAB-MS calcd for C19H23N2O6 (M+H)+: 375.1556, found: 375.1579.
N-[2-(4-Hydroxy-1-methoxymethoxybutyl)phenyl]-4-iodobenzamide (6d)
As a white powder, 6d (643 mg, 87%) was obtained by the same treatment of 12 (500 mg, 1.6 mmol) with
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4-iodobenzoyl chloride (646 mg, 2.4 mmol) as the case of 6b. mp 96-99 °C (Et2O-hexane). H NMR
(CDCl3) δ (ppm): 1.33-1.97 (4H, m, including 1.37, t, J = 5.3 Hz), 1.99-2.18 (1H, m), 3.40 (3H, s),
3.54-3.68 (2H, m), 4.66 (1H, d, J = 6.8 Hz), 4.69 (1H, d, J = 6.8 Hz), 4.74 (1H, t, J = 7.3 Hz), 7.05-7.21 (2H,
m), 7.30-7.42 (1H, m), 7.61-7.72 (2H, m), 7.81-7.93 (2H, m), 8.37 (1H, d, J = 8.0 Hz), 9.75 (1H, br s). 13C
NMR (CDCl3) δ (ppm): 29.2, 31.5, 56.1, 62.2, 79.3, 94.5, 98.9, 122.6, 124.4, 128.6, 128.9, 129.0, 129.2,
134.2, 136.5, 138.0, 164.3. IR (KBr): 3417, 3227, 2943, 1645, 1536, 1494, 1322, 1098, 1062, 1036, 966,
761 cm-1. HRFAB-MS calcd for C19H23NO4I (M+H)+: 456.0672, found: 456.0657.
N-[2-(4-Hydroxy-1-methoxymethoxybutyl)phenyl]-4-(o-toluoylamino)benzamide (6e)
As a colorless amorphous solid, 6e (535 mg, 72%) was obtained by the same treatment of 12 (500 mg, 1.6
mmol) with 4-(o-toluoylamino)benzoyl chloride (663 mg, 2.4 mmol) as the case of 6b. 1H NMR (CDCl3) δ
(ppm): 1.40-1.98 (4H, m), 2.00-2.19 (1H, m), 2.52 (3H, s), 3.42 (3H, s), 3.53-3.67 (2H, m), 4.67 (1H, d, J =
6.8 Hz), 4.70 (1H, d, J = 6.8 Hz), 4.76 (1H, t, J = 7.3 Hz), 7.04-7.21 (2H, m), 7.22-7.45 (4H, m), 7.51 (1H,
d, J = 7.8 Hz), 7.72-7.86 (3H, m), 7.89-8.00 (2H, m), 8.37 (1H, d, J = 8.0 Hz), 9.77 (1H, br s). 13C NMR
(CDCl3) δ (ppm): 19.8, 29.2, 31.5, 56.0, 62.1, 79.1, 94.4, 119.6, 122.8, 124.3, 125.8, 126.7, 128.1, 128.7,
129.0, 129.6, 130.1, 130.5, 131.2, 135.9, 136.5, 136.6, 141.4, 164.6, 168.5. IR (KBr): 3294, 2946, 1659,