Reaktion #165721

Reaktionsgleichung

mixture

N-(5-tert-butylthiazol-2-yl)-5-chloro-2-methoxybenzamide

(S)-(2-oxo-oxazolidin-4-yl)methyl 4-methylbenzenesulfonate

potassium carbonate

→

title compound

Ausbeute 42.9%

N-[(2Z)-5-tert-butyl-3-{[(4S)-2-oxo-1,3-oxazolidin-4-yl]methyl}-1,3-thiazol-2(3H)-ylidene]-5-chloro-2-methoxybenzamide

Ausbeute 42.9%

Lösungsmittel

toluene

Reaktionsbedingungen

Aufarbeitung

1. 1
   WaschenThe mixture was washed with water, brine
2. 2
   Trocknendried with MgSO4
3. 3
   Filtrationfiltered
4. 4
   Einengenconcentrated under reduced pressure
5. 5
   SonstigeThe residue was purified by chromatography over silica gel (EtOAc as eluent)

Vorschrift

A mixture of Example 244A (180 mg, 0.55 mmol), (S)-(2-oxo-oxazolidin-4-yl)methyl 4-methylbenzenesulfonate (180 mg, 0.67 mmol), potassium carbonate (153 mg, 1.1 mmol), tetrabutylammonium iodide (10 mg, 0.03 mmol), tetrabutylammonium hydrogen sulfate (10 mg, 0.03 mmol) and tetraethylammonium iodide (10 mg, 0.04 mmol) in toluene (35 mL) was refluxed for 14 h. The mixture was washed with water, brine, dried with MgSO4, filtered, and concentrated under reduced pressure. The residue was purified by chromatography over silica gel (EtOAc as eluent) to afford 100 mg of the title compound. 1H NMR (300 MHz, CDCl3) δ ppm 1.36 (s, 9H), 3.92 (s, 3H), 4.11-4.26 (m, 2H), 4.30-4.41 (m, 2H), 4.57 (t, J=8.6 Hz, 1H), 6.33 (s, 1H), 6.62 (s, 1H), 6.93 (d, J=8.8 Hz, 1H), 7.35 (dd, J=9.0, 2.9 Hz, 1H), 7.79 (d, J=2.7 Hz, 1H). MS (DCI/NH3) m/z 424 (M+H)+.

Quelle