Boron trifluoride etherate → HCID 86728134, compound

Participants

Reaction Conditions

Reaction Steps

A solution of tert-butyl N-tert-butoxycarbonyl-N-[(3R)-3-(2-fluoro-5-nitro-phenyl)-3,6,6-trimethyl-1,1-dioxo-2H-1,4-thiazin-5-yl]carbamate (0.4 g, 0.756 mmol) in THF (3.8 mL) was cooled to −78° C. and to this was added LHMDS (1.0M in THF; 1.51 ml, 1.51 mmol) dropwise via syringe. The reaction was stirred at −78° C. for 1 hr. 2,2-dimethyloxirane (0.134 ml, 1.51 mmol) was then added followed by BF3.OEt2 (1.44 ml, 1.44 mmol) as a solution in 2 mL of THF. The reaction was stirred at −78° C. for 1 hr. The reaction was treated with aqueous ammonium chloride solution and extracted with ethyl acetate. The organic portion was dried over Na2SO4, filtered, concentrated and purified by column chromatography, eluting with 0-40% EtOAc/Heptanes to give the title compound (376 mg, 0.624 mmol, 83% yield) as a white solid. MS m/z=624.2 (M+Na).

Provenance & Evidence