Reaktion #339957

Reaktionsgleichung

295

(2-{4-[1-Hydroxy-2-(3,4,5-trimethoxy-phenylamino)-ethyl]-benzoylamino}-phenyl)-carbamic acid tert-butyl ester

1,1′-carbonyldiimidazole

→

desired compound

Ausbeute 58.0%

N-(2-Amino-phenyl)-4-[2-oxo-3-(3,4,5-trimethoxy-phenyl)-oxazolidin-5-yl]-benzamide

Ausbeute 58.0%

Lösungsmittel

DCM

Reaktionsbedingungen

Aufarbeitung

1. 1
   SonstigeDCM was removed under reduced pressure, AcOEt
2. 2
   workup.ADDITIONa solution of sat. NH4Cl were added
3. 3
   Sonstigethe phases were separated
4. 4
   WaschenThe organic layer was washed with brine
5. 5
   Trocknendried over anhydrous Na2SO4
6. 6
   Filtrationfiltered
7. 7
   Einengenconcentrated
8. 8
   SonstigeThe crude residue was purified by flash chromatography on silica gel (Hexane/AcOEt: 30/70)

Vorschrift

To a solution of 295 (130 mg, 0.242 mmol) in DCM (2 mL) was added 1,1′-carbonyldiimidazole (47 mg, 0.29 mmol) and the mixture was stirred at room temperature for 16 h. DCM was removed under reduced pressure, AcOEt and a solution of sat. NH4Cl were added and the phases were separated. The organic layer was washed with brine, dried over anhydrous Na2SO4, filtered and concentrated. The crude residue was purified by flash chromatography on silica gel (Hexane/AcOEt: 30/70) to afford the desired compound (80 mg, 0.14 mmol, 58% yield). 1H NMR (DMSO) δ (ppm): 9.39 (s, 1H), 8.04 (d, J=8.1 Hz, 2H), 7.84 (d, J=7.5 Hz, 1H), 7.52 (d, J=8.1 Hz, 2H), 7.26-7.12 (m, 3H), 6.86-6.74 (m, 3H), 5.70 (t, J=8.4 Hz, 1H), 4.24 (t, J=8.7 Hz, 1H), 3.97-3.87 (m, 1H), 3.87 (s, 6H), 3.82 (s, 3H), 1.52 (s, 9H).

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