Reaktion #357262

Reaktionsgleichung

(2S)-oxiran-2-ylmethyl-3-nitrobenzenesulfonate

N-cyclopropyl-2-hydroxy-4-(trityloxy)benzamide

cesium carbonate

Cs2CO3

→

subtitled compound

Ausbeute 70.9%

N-Cyclopropyl-2-[(2S)-oxiran-2-ylmethoxy]4-(trityloxy)benzamide

Ausbeute 70.9%

Lösungsmittel

dimethylformamide

Reaktionsbedingungen

Aufarbeitung

1. 1
   SonstigeThe reaction mixture was partitioned between ethyl acetate and water
2. 2
   TrocknenThe organic layer was dried over sodium sulphate, Na2SO4
3. 3
   Filtrationfiltered
4. 4
   Einengenconcentrated
5. 5
   Sonstigethe residue was purified by silica gel flash chromatography (0-40% ethyl acetate in petroleum ether)

Vorschrift

A mixture of (2S)-oxiran-2-ylmethyl-3-nitrobenzenesulfonate (119 mg, 0.459 mmol), N-cyclopropyl-2-hydroxy-4-(trityloxy)benzamide (200 mg, 0.459 mmol) and cesium carbonate, Cs2CO3, (186.2 mg, 0.573 mmol) in dimethylformamide (3 mL) was kept on stirring at room temperature overnight. The reaction mixture was partitioned between ethyl acetate and water. The organic layer was dried over sodium sulphate, Na2SO4, filtered, concentrated and the residue was purified by silica gel flash chromatography (0-40% ethyl acetate in petroleum ether) to give the subtitled compound (160 mg).

Quelle