Benzyl Bromide → HCID 10813914, compound

Participants

Reaction Steps

A mixture of ethyl (RS)-2-tert-butoxycarbonylamino-3-(5-ethoxycarbonyl-3-hydroxyisoxazol-4-yl)propionate (3.2 g, 8.6 mmol), K2CO3 (2.4 g, 17.2 mmol) in acetone (40 mL) was heated to reflux temperature. Benzyl bromide (2.2 g, 12.9 mmol) was added, and the mixture was boiled under reflux for 1.5 h. Concentrated in vacuo and subjected to flash chromatography (SiO2, eluent: heptane/ethyl acetate (2:1)) to give ethyl (RS)-2-[(tert-butoxycarbonyl)amino]-3-[3-benzyloxy-5-(ethoxycarbonyl)isoxazol-4-yl]propionate (1.64 g, 41%) and ethyl (RS)-2-[(tert-butoxycarbonyl)amino]-3-(2-benzyl-5-ethoxycarbonyl-2,3-dihydro-3-oxoisoxazol-4-yl)propionate (0.7 g, 18%).

Provenance & Evidence