Pyridine → (S)-2-(tert-butoxycarbonylamino)-1-cyclohexylpentan-3-yl 4-methylbenzenesulfonate

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To a mixture of (S)-tert-butyl 1-cyclohexyl-3-hydroxypentan-2-ylcarbamate (1.067 g, 3.74 mmol), catalytic amount of DMAP, and pyridine (0.651 g, 8.24 mmol) at 0° C. was added TsCl (0.856 g, 4.49 mmol) in CH2Cl2 (4 mL) over 2 min. The resulting solution was stirred at rt overnight. The reaction mixture was diluted with EtoAc, washed with 1 M HCl, sat. aq. NaHCO3, brine, dried over Na2SO4 and filtered. The filtrate was concentrated and purified by on silica gel chromatography to give (S)-2-(tert-butoxycarbonylamino)-1-cyclohexylpentan-3-yl 4-methylbenzenesulfonate as a white solid. MS ESI +ve m/z 462 (M+Na).

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