반응 단계
The procedure is the same as in Example 45 except that the dihydrochloride of 3-(3-fluoro-4-morpholinylphenyl-5-aminomethyl-1,3-oxazolidin-2-one (5a) was replaced by dihydrochloride of 3-(3-fluoro-4-morpholinylphenyl)-5(S)-aminomethyl-1,3-oxazolidin-2-one ((S)-5b) to obtain (S)—N-((3-(3-fluoro-4-(4-morpholinyl)phenyl)-2-oxo-5-oxazolidinyl)methyl)acetamide (Linezolid) having a melting point of 78-179° C. and at a yield of 90%; [∝]D20=−9.1° (c 1.0, CHCl3); 1H NMR(CDCl3, 400 MHz) δ 7.43 (dd, J1=2.8 Hz, J2=14.4 Hz, 1H, Ar—H), 7.06 (dd, J1=1.6 Hz, J2=8.8 Hz, 1H, Ar—H), 6.94 (t, J=9.2 Hz, 1H, Ar—H), 6.17 (t, J1=6.0 Hz, 1H, NH), 4.80-4.74 (m, IH, CHO), 4.02 (t, J=8.8 Hz, 1H, CH2CHO), 3.86 (t, J=4.8 Hz, 4H, 2×OCH2), 3.75 (dd, J1=6.8 Hz, J2=8.8 Hz, 1H, CH2CHO), 3.71-3.58 (m, 2H, CH2NH), 3.06 (t, J=4.8 Hz, 4H, 2×NCH2), 2.02 (s, 3H, CH3CO); 13C NMR (CDCl3, 100 MHz) 171.4, 155.7 (d, J=245 Hz), 154.5, 136.4 (d, J=8.8 Hz), 132.8 (d, J=10.4 Hz), 118.6 (d, J=3.9 Hz), 113.8 (d, J=3.0 Hz), 107.4 (d, J=26.1 Hz), 72.0, 66.8, 50.8, 47.5, 41.7, 22.8; HR-TOF-MS (+Q) m/z: 338.1518 (Calculated [C16H20FN3O4+H]+: 338.1516).
