Hydrochloric Acid → (S)-methyl 2-(methylsulfonyloxy)-2-phenylacetate

Participants

Reaction Steps

To a solution of (S)-methyl 2-hydroxy-2-phenylacetate (20.0 g, 120 mmol) in DCM (240 mL) maintained at 0° C. under N2 flowstream, are added mesylchloride (11.2 mL, 144 mmol) and TEA (20.1 mL, 144 mmol) and the mixture is stirred at RT for 1 hour (UPLC-MS monitoring: complete conversion). The mixture is cooled to 0° C., 0.1N HCl (240 mL) is added and the desired compound is extracted with DCM (2×200 mL). The combined DCM phases are dried over Na2SO4, filtered and evaporated to dryness. The resulting crude is purified by filtration through a silica bed eluting with DCM, obtaining 22.4 g of the title compound as white solid (76% yield).

Provenance & Evidence