4-Toluenesulfonyl chloride → HCID 86748025, compound

Participants

Reaction Conditions

Reaction Steps

BOC-(2-isobutyl)-3-hydroxypropyl glycine benzyl ester (0.17 g, 0.45 mmol) is dissolved in pyridine (2 ml), cooled to 0° C., and p-toluenesulfonyl chloride (0.25 g, 1.31 mmol) is added. The mixture is then stirred at room temperature for 16 hours, diluted with ether, and the organic layer washed with 1N HCl, 10% copper sulfate solution, brine. The organic layer is dried over magnesium sulfate, filtered, concentrated in vacuo to give the tosylated product. The primary tosylate (0.23 g, 0.43 mmol) is dissolved in DMF/water (10:1) (2 ml) and sodium azide (0.29 g, 4.46 mmol) is added. The mixture is heated at 90° C. for four hours, cooled, diluted with ether and poured into brine. The organic layer is washed with water, brine, dried over magnesium sulfate, filtered, and concentrated in vacuo. The crude product is purified by flash chromatography, eluting with 10% ethyl aceate in hexanes to give BOC-(2-isobutyl)-3-azidopropyl glycine benzyl ester.

Provenance & Evidence