Реакция #5517

Уравнение реакции

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

Растворители

dimethylformamide

Условия реакции

Обработка

1. 1
   Экстракцияextracted with ethyl acetate (2×100 ml)
2. 2
   ПромывкаThe combined organic layers are washed with water (2×100 ml), brine (1×200 ml)
3. 3
   Сушкаdried (MgSO4)
4. 4
   Другоеthe solvent is evaporated

Методика

(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.

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