Imidazole → HCID 59279535, compound

Participants

Reaction Steps

A solution of tert-butylchlorodimethylsilane (661 mg, 4.38 mmol) in DMF (2.5 mL) was added dropwise to a stirred solution of (S)-methyl 2-hydroxy-3-methoxypropanoate C4a (490 mg, 3.65 mmol) and 1H-imidazole (497 mg, 7.31 mmol) in DMF (5 mL) at 20° C., over a period of 2 minutes. The resulting solution was stirred at ambient temperature for 3 hours. The reaction mixture was concentrated, diluted with EtOAc (50 mL) and washed sequentially with water (4×15 mL) and saturated brine (20 mL). The organic layer was dried over MgSO4, filtered and evaporated to afford crude product. Purification by flash silica chromatography, elution gradient 20 to 50% EtOAc in isohexane afforded (S)-methyl 2-(tert-butyldimethylsilyloxy)-3-methoxypropanoate (750 mg).

Provenance & Evidence