4-(Bromomethyl)-5-methyl-1,3-dioxol-2-one → HCID 86628923, compound

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Reaction Steps

Following the general procedure for the preparation of acyloxyalkyl/alkoxycarbonyloxyalkyl carboxylic esters from carboxylic acids of Description 22, (2R)-4-{[3-(acetylamino)propyl]sulfonyloxy}-3,3-dimethyl-2-(1,1,2,2-tetramethyl-1-silapropoxy)butanoic acid (19) (1.5 g, 3.5 mmol) dissolved in 15 mL of anhydrous toluene was reacted with 1.4 g (7.0 mmol) of commercially available 5-bromomethyl-4-methyl-1,3-dioxolen-2-one in the presence of 1.4 g (5.3 mmol) of silver carbonate (Ag2CO3). After work-up and further purification by mass-guided preparative HPLC, 0.1 g (5.3% yield) of the title compound (48a) was obtained as a colorless, viscous oil. Rf=0.62 (EtOAc/MeOH=19:1). MS (ESI) m/z 538.14 (M+H)+, 560.13 (M+Na)+. The analytical data was consistent with the proposed structure.

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