Acetic Anhydride → (3R,4S,5R)-4-acetylamino-3-(1-ethyl-propoxy)-5-methanesulfonyloxy-cyclohex-1-enecarboxylic acid ethyl ester

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Reaction Steps

To a solution of 190 mg of 20 and EtOAc (1.6 mL) in a 10 mL round-bottom flask equipped with a magnetic stirrer and an inert gas supply was added was added at RT aqueous 1 M sodium hydrogen carbonate (1.6 mL). To the resulting mixture was added 62 μl of acetic anhydride and the 2-phase mixture was stirred for 1 h at RT. The mixture was diluted with 2.0 mL of EtOAc, the organic phase was separated, dried (Na2SO4), filtered and the filter cake was washed with total 3.0 mL EtOAc. The filtrate was evaporated at 40° C./200-10 mbar to afford 192 mg of 22 as off white crystals.

Provenance & Evidence