Реакция #5497

Уравнение реакции

Trans 3-(acetylthiomethyl)-2-oxo-1-azacyclodecane-10-carboxylic acid

Benzyl bromide

cesium carbonate

→

trans benzyl 3-(acetylthiomethyl)-2-oxo-1-aza-cyclodecane-10-carboxylate

Растворители

dimethylformamide

water

Условия реакции

Обработка

1. 1
   Экстракцияthe aqueous layer is extracted several times with methylene chloride
2. 2
   СушкаThe combined organic layers are dried (MgSO4)
3. 3
   Другоеthe solvent is evaporated
4. 4
   ДругоеThe product is purified by silica gel chromatography (10% ethyl acetate/hexane)

Методика

Trans 3-(acetylthiomethyl)-2-oxo-1-azacyclodecane-10-carboxylic acid (0.15 g, 0.52 mmol) is dissolved in dimethylformamide (2.5 mL). Benzyl bromide (0.062 mL, 0.52 mmol) and cesium carbonate (0.085 g, 0.26 mmol) are added, and the reaction is stirred at room temperature overnight. The reaction is diluted with water, and the aqueous layer is extracted several times with methylene chloride. The combined organic layers are dried (MgSO4), and the solvent is evaporated. The product is purified by silica gel chromatography (10% ethyl acetate/hexane) to give trans benzyl 3-(acetylthiomethyl)-2-oxo-1-aza-cyclodecane-10-carboxylate m.p. 117°-118° C.

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