4-Toluenesulfonyl chloride → 3-[(tert-Butoxycarbonyl)amino]propyl 4-methylbenzene-1-sulfonate

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Reaction Steps

3-(t-Butoxycarbonylamino)propanol (10.0 g) is dissolved in methylene chloride (100 ml), and thereto are added with stirring triethylamine (8.66 g) and tosyl chloride (16.3 g) under ice-cooling, and the reaction mixture is stirred at room temperature overnight. The reaction mixture is concentrated, and the residue is dissolved in a mixture of water and ethyl acetate. The organic layer is separated, washed with a saturated sodium chloride solution, dried over sodium sulfate, and concentrated under reduced pressure. The residue is purified by silica gel column chromatography to give the title compound (15.37 g) as a pale yellow oil.

Provenance & Evidence