ChemicalBook CAS DataBase List Linezolid

Linezolid synthesis

8synthesis methods

Product Name:Linezolid
CAS Number:165800-03-3
Molecular formula:C16H20FN3O4
Molecular Weight:337.35

108-24-7
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$14.00/250ML

168828-90-8 Synthesis

(S)-N-[[3-[3-Fluoro-4-(4-morpholinyl)phenyl]-2-oxo-5-oxazolidinyl]methyl]amine

168828-90-8
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$7.00/100mg

165800-03-3
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$5.00/100mg

Yield:165800-03-3 98%

Reaction Conditions:

with triethylamine in dichloromethane at 20; for 3 h;

Steps:

8. Synthesis of compound 1, Linezolid

Compound 9 (100 mg, 0.34 mmol) was dissolved into 5 mL of anhydrous dicholoromethane in a 25 mL round bottom flask. The mixture was treated with Ac₂O (0.2 mL, 1.59 mmol) and TEA (0.28 mL, 2.0 mmol) at room temperature. After 3 hours, dilute the mixture with EtOAc (40 mL).Wash the mixture with HCl (0.1 M, 5 mL), Sat. NaHCO₃ (10) and brine (10 mL).Dry the organic layer with Na₂SO₄. Filter the organic layer and concentrate the organic layer at reduced pressure, the desired product was purified by silica gel column. Yield, 129 mg, 98%. ¹H NMR (400 MHz, DMSO-d6) δ 8.27 (s, 1H), 7.49 (d, J = 15.0 Hz, 1H), 7.18 (d, J = 8.6 Hz, 1H), 7.04 (t, J = 9.2 Hz, 1H), 4.72 (s, 1H), 4.08 (t, J = 8.8 Hz, 1H), 3.71 (m, 4H), 2.95 (m, 4H), 1.85 (s, 3H). ¹³C NMR (101 MHz, DMSO-d6) δ 170.51, 156.26, 154.51, 153.83, 135.96 (d, J = 8.8 Hz), 133.89 (d, J = 10.6 Hz), 119.60 (d, J = 4.0 Hz), 114.42 (d, J = 2.6 Hz), 107.16, 106.90, 72.03, 66.61, 51.14, 47.73, 41.88, 22.87. ¹⁹F NMR (376 MHz, DMSO) δ -121.26.

References:

Wang, Keyin;Chen, Yinzhe;Wang, Siyuan;Zhang, Qian [Tetrahedron Letters,2022,vol. 105,art. no. 154050] Location in patent:supporting information

75-36-5 Synthesis