Chloride → 1,3-Di(tert-butyloxycarbonylamino)-2-(p-toluenesulfonyloxy)propane

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Reaction Steps

1,3-di(tert-butyloxycarbonylamino)propan-2-ol (example 10a) (2.89 g, 10 mmol) and triethylamine (2.22 ml, 16 mmol) were dissolved in anhydrous dichloromethane (100 ml). The reaction mixture was cooled in an ice bath followed by dropwise addition of tosyl chloride (2.272 g, 12 mmol) dissolved in dichloromethane (30 ml). The reaction mixture was then stirred at room temperature for 72 hours. One equivalent of chloride and 1.6 of triethylamine were added after 48 hours. Water was added to stop the reaction and the medium was allowed to settle. The organic phase was washed several times with water. The aqueous phases were combined and extracted again with dichloromethane. The organic phase was dried on magnesium sulfate, filtered and the solvent was evaporated. The residue obtained (6.44 g) was purified by chromatography on silica gel (eluent:dichloromethane followed by dichloromethane/methanol 99:1) to yield the desired compound as a white solid.

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