[OH:1][CH2:2][C@H:3]([CH3:8])[C:4]([O:6][CH3:7])=[O:5].[CH3:9][S:10](Cl)(=[O:12])=[O:11].CCN(CC)CC>C(Cl)Cl>[CH3:9][S:10]([O:1][CH2:2][C@H:3]([CH3:8])[C:4]([O:6][CH3:7])=[O:5])(=[O:12])=[O:11]A solution of methyl 3-hydroxy-2-(S)-methylpropanoate (35 g, 295 mmol) in 830 mL of CH2Cl2, under N2 atmosphere, was cooled to -60° C. With rapid stirring, methanesulfonyl chloride (24 mL, 310 mmol) was added, followed by Et3N (50 mL, 354 mmol) over 90 s. As the addition ended, a heavy white precipitate formed which stopped the magnetic stirring. The cold bath was removed and the reaction allowed to reach r.t. The reaction mixture was poured into aq 25% NH4OAc. After separation, the organic phase was dried over MgSO4 and evaporated to give the title compound as a colorless oil (59.1 g, 102%).
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