反応 #50272

反応方程式

water

cesium carbonate

(3R)-6-(Pivaloylthiomethyl)-5-oxo-1thia-4-azacyclotridecane-3-carboxylic acid

benzyl bromide

→

benzyl (3R)-6-(pivaloylthiomethyl)-5-oxo-1-thia-4-azacyclotridecane-3-carboxylate

溶媒

dimethylformamide

反応条件

後処理

1. 1
   抽出extracted with ethyl acetate (2×100 ml)
2. 2
   洗浄The combined organic layers are washed with water (2×100 ml), brine (1×200 ml)
3. 3
   乾燥dried (MgSO4)
4. 4
   その他the solvent is evaporated

実験手順

(3R)-6-(Pivaloylthiomethyl)-5-oxo-1thia-4-azacyclotridecane-3-carboxylic acid (0.25 g, 0.64 mmol) is dissolved in dimethylformamide (5 ml) and cesium carbonate (0.23 g, 0.71 mmol) is added, followed by benzyl bromide (0.11 g, 0.64 mmol). The mixture is stirred overnight at room temperature, poured into water (300 ml) and extracted with ethyl acetate (2×100 ml). The combined organic layers are washed with water (2×100 ml), brine (1×200 ml), dried (MgSO4) and the solvent is evaporated. Silica gel chromatography (3% ethyl acetate/hexane) gives benzyl (3R)-6-(pivaloylthiomethyl)-5-oxo-1-thia-4-azacyclotridecane-3-carboxylate, m.p. 135°-137° C.

出典