[C:1]([O:5][C:6](=[O:15])[NH:7][C@H:8]1[CH2:13][CH2:12][C@@H:11]([OH:14])[CH2:10][CH2:9]1)([CH3:4])([CH3:3])[CH3:2].C(N(CC)CC)C.[CH3:23][S:24](Cl)(=[O:26])=[O:25].O>C(Cl)Cl>[C:1]([O:5][C:6]([NH:7][C@@H:8]1[CH2:9][CH2:10][C@H:11]([O:14][S:24]([CH3:23])(=[O:26])=[O:25])[CH2:12][CH2:13]1)=[O:15])([CH3:4])([CH3:2])[CH3:3]A solution of cis (4-hydroxy-cyclohexyl)-carbamic acid tert-butyl ester (1.00 g, 4.70 mmol) in DCM (10 mL) was treated with triethylamine (1.29 mL, 9.30 mmol) and the mixture was cooled to 0° C. Methanesulfonyl chloride (0.54 mL, 7.00 mmol) was added dropwise and the mixture was stirred at 0° C. for 15 minutes. Water was added and the phases were separated. The aqueous phase was extracted with DCM (×2) and the combined organic phase was washed with saturated sodium hydrogen carbonate solution, and brine, dried with sodium sulfate and concentrated under vacuum to give 1.39 g (quant) of Cis methanesulfonic acid 4 tert-butoxycarbonylamino-cyclohexyl ester as a peach coloured solid which was used without further purification. 1H NMR (400 MHz, CDCl3) δ: 4.89 (m, 1H), 4.46 (br s, 1H), 3.53 (br s, 1H), 3.01 (s, 3H), 2.05 (m, 2H), 1.84-(m, 2H), 1.73 (m, 2H), 1.58 (m, 2H), 1.45 (s, 9H).
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