تفاعل #5517

معادلة التفاعل

water

cesium carbonate

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

benzyl bromide

→

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

المذيبات

dimethylformamide

ظروف التفاعل

المعالجة

1. 1
   استخلاصextracted with ethyl acetate (2×100 ml)
2. 2
   غسيلThe combined organic layers are washed with water (2×100 ml), brine (1×200 ml)
3. 3
   تجفيفdried (MgSO4)
4. 4
   أخرىthe solvent is evaporated

الإجراء التجريبي

(3R)-6-(Pivaloylthiomethyl)-5-oxo-1-thia-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.

المصدر