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

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Reaction Steps

To a solution of 2.95 g (16.9 mmoles) of 3-tert-butoxycarbonylamino-1-propanol in 50 ml of pyridine, while being cooled in ice under an argon atmosphere, was added dropwise over a period of 40 minutes a pyridine solution containing 3.36 g (17.7 mmoles) of p-toluenesulfonyl chloride. The mixture was left standing overnight at 7° C., then admixed with a small volume of water and evaporated to dryness. The residue was dissolved in 200 ml of chloroform, washed successively with 5% aqueous potassium hydrogensulfate solution, saturated aqueous sodium hydrogencarbonate solution and water, then dried over anhydrous sodium sulfate and evaporated to dryness. The residue was subjected to column chromatography using 120 g of silica gel (Wakogel® C-200) and a toluene-ethyl acetate (8:1 by volume) mixture as developing solvent (15 ml fraction size). Fractions No. 35 to No. 68 were combined and evaporated to dryness to yield 3.06 g (55% yield) of O-tosyl-3-tert-butoxycarbonylamino-1-propanol, a colorless oily substance.

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