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Arch. Pharm. Chem. Life Sci. 2005, 338, 147−158
Methyl-4-[3-(4-isopropylphenyl)-2-oxo-5-oxazolidinyl]methoxy-
benzoate (3m)
Hz), 4.94Ϫ5.03 (1H, m), 6.92 (2H, d, J ϭ 9.2 Hz), 6.93 (2H, d, J ϭ
8.9 Hz), 7.46 (2H, d, J ϭ 8.9 Hz), 8.00 (2H, d, J ϭ 9.2 Hz). Anal.
Calcd. for C19H19NO6: C, 63.86; H, 5.36; N, 3.92. Found: C, 63.83;
H, 5.37; N, 3.97.
1H-NMR (CDCl3) δ: 1.24 (6H, d, J ϭ 6.9 Hz), 2.82-2.96 (1H, m),
3.89 (3H, s), 4.05 (1H, dd, J ϭ 8.9, 5.9 Hz), 4.21 (1H, dd, J ϭ 8.9,
8.9 Hz), 4.27 (2H, d, J ϭ 4.6 Hz), 4.95Ϫ5.04 (1H, m), 6.93 (2H, d,
J ϭ 8.9 Hz), 7.25 (2H, d, J ϭ 8.6 Hz), 7.48 (2H, d, J ϭ 8.6 Hz),
8.00 (2H, d, J ϭ 8.9 Hz). Anal. Calcd. for C21H23NO5: C, 68.28; H,
6.28; N, 3.79. Found: C, 68.26; H, 6.30; N, 3.95.
Methyl 4-[3-(4-ethoxyphenyl)-2-oxo-5-oxazolidinyl]methoxybenzo-
ate (3t)
1H-NMR (CDCl3) δ: 1.36 (3H, t, J ϭ 6.9 Hz), 3.89 (3H, s),
3.97Ϫ4.19 (4H, m), 4.27 (2H, d, J ϭ 5.0 Hz), 4.95Ϫ5.05 (1H, m),
6.92Ϫ7.02 (4H, m), 7.23Ϫ7.41 (2H, m), 8.01 (2H, d, J ϭ 8.9 Hz).
Methyl-4-[3-(4-n-butylphenyl)-2-oxo-5-oxazolidinyl]methoxy-
benzoate (3n)
Methyl-4-[3-(4-isopropoxyphenyl)-2-oxo-5-oxazolidinyl]methoxy-
benzoate (3u)
1H-NMR (CDCl3) δ: 0.92 (3H, t, J ϭ 7.3 Hz), 1.27-1.42 (2H, m),
1.52-1.64 (2H, m), 2.60 (2H, t, J ϭ 7.6 Hz), 3.89 (3H, s), 4.04 (1H,
dd, J ϭ 8.9, 5.9 Hz), 4.20 (1H, dd, J ϭ 8.9, 8.9 Hz), 4.27 (2H, d,
J ϭ 4.6 Hz), 4.94Ϫ5.04 (1H, m), 6.93 (2H, d, J ϭ 8.9 Hz), 7.20
(2H, d, J ϭ 8.9 Hz), 7.46 (2H, d, J ϭ 8.9 Hz), 8.00 (2H, d, J ϭ 8.9
Hz). Anal. Calcd. for C22H25NO5: C, 68.91; H, 6.57; N, 3.65.
Found: C, 68.88; H, 6.62; N, 3.65.
1H-NMR (CDCl3) δ: 1.33 (6H, d, J ϭ 6.3 Hz), 3.89 (3H, s), 4.02
(1H, dd, J ϭ 8.9, 5.9 Hz), 4.19 (1H, dd, J ϭ 8.9, 8.9 Hz), 4.27 (2H,
d, J ϭ 4.6 Hz), 4.47Ϫ4.56 (1H, m), 4.94Ϫ5.03 (1H, m), 6.91 (2H,
d, J ϭ 8.9 Hz), 6.93 (2H, d, J ϭ 8.9 Hz), 7.44 (2H, d, J ϭ 8.9 Hz),
8.01 (2H, d, J ϭ 8.9 Hz). Anal. Calcd. for C21H23NO6: C, 65.44; H,
6.01; N, 3.63. Found: C, 65.40; H, 6.20; N, 3.85.
Methyl-4-[3-(4-isobutylphenyl)-2-oxo-5-oxazolidinyl]methoxy-
benzoate (3o)
Methyl-4-[3-(4-trifluoromethoxyphenyl)-2-oxo-5-oxazolidinyl]-
methoxybenzoate (3v)
1H-NMR (CDCl3) δ: 0.90 (6H, d, J ϭ 6.6 Hz), 1.79Ϫ1.90 (1H, m),
2.46 (2H, d, J ϭ 7.3 Hz), 3.89 (3H, s), 4.05 (1H, dd, J ϭ 8.9, 6.1
Hz), 4.22 (1H, dd, J ϭ 8.9, 8.9 Hz), 4.27Ϫ4.34 (2H, m), 4.97Ϫ5.05
(1H, m), 6.94 (2H, d, J ϭ 8.9 Hz), 7.16 (2H, d, J ϭ 8.6 Hz), 7.46
(2H, d, J ϭ 8.6 Hz), 8.00 (2H, d, J ϭ 8.9 Hz). Anal. Calcd. for
C22H25NO5: C, 68.91; H, 6.57; N, 3.65. Found: C, 68.91; H, 6.60;
N, 3.63.
1H-NMR (CDCl3) δ: 3.89 (3H, s), 4.08 (1H, dd, J ϭ 8.9, 5.9 Hz),
4.22 (1H, dd, J ϭ 8.9, 8.9 Hz), 4.27Ϫ4.31 (2H, m), 5.00Ϫ5.06 (1H,
m), 6.93 (2H, d, J ϭ 8.9 Hz), 7.26 (2H, d, J ϭ 9.2 Hz), 7.61 (2H,
d, J ϭ 9.2 Hz), 8.01 (2H, d, J ϭ 8.9 Hz). Anal. Calcd. for
C
19H16F3NO6: C, 55.48; H, 3.92; N, 3.41. Found: C, 55.47; H, 3.87;
N, 3.41.
Methyl-4-[3-(4-tert-butylphenyl)-2-oxo-5-oxazolidinyl]methoxy-
benzoate (3p)
Methyl-4-[3-(2,4-dimethoxyphenyl)-2-oxo-5-oxazolidinyl]methoxy-
benzoate (3w)
1H-NMR (CDCl3) δ: 1.32 (9H, s), 3.89 (3H, s), 4.05 (1H, dd, J ϭ
8.9, 5.9 Hz), 4.21 (1H, dd, J ϭ 8.9, 8.9 Hz), 4.27 (2H, d, 4.6 Hz),
4.95Ϫ5.04 (1H, m), 6.93 (2H, d, J ϭ 8.9 Hz), 7.41 (2H, d, J ϭ 8.9
Hz), 7.49 (2H, d, J ϭ 8.9 Hz), 8.00 (2H, d, J ϭ 8.9 Hz). Anal.
Calcd. for C22H25NO5: C, 68.91; H, 6.57; N, 3.65. Found: C, 68.97;
H, 6.69; N, 3.69.
1H-NMR (CDCl3) δ: 3.81 (6H, s), 3.84Ϫ3.90 (1H, m), 3.90 (3H, s),
4.10 (1H, dd, J ϭ 8.7, 8.7 Hz), 4.27 (2H, d, J ϭ 5.0 Hz), 4.94Ϫ5.03
(1H, m), 6.48Ϫ6.53 (2H, m), 6.96 (2H, d, J ϭ 8.9 Hz), 7.24Ϫ7.23
(1H, m), 8.02 (2H, d, J ϭ 8.9 Hz). Anal. Calcd. for C20H21NO7: C,
62.01; H, 5.46; N, 3.62. Found: C, 62.06; H, 5.47; N, 3.61.
Methyl-4-[3-(4-nitrophenyl)-2-oxo-5-oxazolidinyl]methoxy-
benzoate (3x)
Methyl-4-[3-(4-trifluoromethyphenyl)-2-oxo-5-oxazolidinyl]-
methoxybenzoate (3q)
1H-NMR (DMSO-d6) δ: 3.82 (3H, s), 4.05 (1H, dd, J ϭ 9.2, 6.1
Hz), 4.34 (1H, dd, J ϭ 9.2, 9.2 Hz), 4.38 (1H, dd, J ϭ 11.2, 6.6
Hz), 4.44 (1H, dd, J ϭ 11.2, 3.3 Hz), 5.17 (1H, m), 7.70 (2H, d,
J ϭ 8.9 Hz), 7.85 (2H, d, J ϭ 9.3 Hz), 7.92 (2H, d, J ϭ 8.9 Hz),
8.31 (2H, d, J ϭ 9.3 Hz). Anal. Calcd. for C18H16N2O7: C, 58.07;
H, 4.33; N, 7.52. Found: C, 58.03; H, 4.30; N, 7.38.
1H-NMR (CDCl3) δ: 3.89 (3H, s), 4.11 (1H, dd, J ϭ 8.9, 5.9 Hz),
4.25 (1H, dd, J ϭ 8.9, 8.9 Hz), 4.26Ϫ4.36 (2H, m), 5.00Ϫ5.09 (1H,
m), 6.92 (2H, d, J ϭ 8.9 Hz), 7.64 (2H, d, J ϭ 8.9 Hz), 7.71 (2H,
d, J ϭ 8.9 Hz), 8.00 (2H, d, J ϭ 8.9 Hz). Anal. Calcd. for
C19H16F3NO5: C, 57.73; H, 4.08; N, 3.54. Found: C, 57.73; H, 3.99;
N, 3.60.
Methyl 4-[3-(4-chlorophenyl)-2-oxo-5-oxazolidinyl]ethoxybenzoate
(3y)
Methyl-4-[3-(4-methoxyphenyl)-2-oxo-5-oxazolidinyl]methoxy-
benzoate (3r)
A mixture of lithium bromide monohydrate (30 mg, 0.3 mmol) and
tri-n-butylphosphine oxide (63 mg, 0.3 mmol) in toluene (5 mL) was
heated to distill the solvent then additional xylene was added. To
the mixture, a solution of 1e (889 mg, 4 mmol) and 2b (614 mg, 4
mmol) in xylene (2 mL) was added at 140°C. The mixture was
stirred at the same temperature for 2 h then evaporated under re-
duced pressure. To the residue EtOH was added and the precipitates
were corrected by suction and washed with EtOH to give 3y as
white solid (1.13 g, 75%). Mp. 139Ϫ141°C; 1H-NMR (CDCl3) δ:
2.27Ϫ2.35 (2H, m), 3.80 (1H, dd, J ϭ 7.7, 7.1 Hz), 3.89 (3H, s),
4.18 (1H, dd, J ϭ 8.6, 8.6 Hz), 4.23Ϫ4.29 (2H, m), 4.92Ϫ4.98 (1H,
m), 6.91 (2H, d, J ϭ 9.2 Hz), 7.34 (2H, d, J ϭ 9.2 Hz), 7.49 (2H,
d, J ϭ 9.2 Hz), 8.00 (2H, d, J ϭ 9.2 Hz).
1H-NMR (CDCl3) δ: 3.82 (3H, s), 3.88 (3H, s), 4.03 (1H, dd, J ϭ
8.9, 5.9 Hz), 4.19 (1H, dd, J ϭ 8.9, 8.9 Hz), 4.23Ϫ4.31 (2H, m),
4.94Ϫ5.03 (1H, m), 6.68Ϫ6.73 (1H, m), 6.92 (2H, d, J ϭ 8.9 Hz),
7.03Ϫ7.08 (1H, m), 7.25Ϫ7.32 (2H, m), 7.99 (2H, d, J ϭ 8.9 Hz).
Anal. Calcd. for C19H19NO6: C, 63.86; H, 5.36; N, 3.92. Found: C,
63.85; H, 5.29; N, 3.94.
Methyl-4-[3-(4-methoxyphenyl)-2-oxo-5-oxazolidinyl]methoxy-
benzoate (3s)
1H-NMR (CDCl3) δ: 3.81 (3H, s), 3.89 (3H, s), 4.02 (1H, dd, J ϭ
8.9, 5.9 Hz), 4.18 (1H, dd, J ϭ 8.9, 8.9 Hz), 4.27 (2H, d, J ϭ 4.6
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