Ammonium Chloride → HCID 90301194, 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 (bis-boc intermediate) (2.03 g, 3.83 mmol)) in THF (24 mL) was cooled to −78° C. LHMDS (1.0 M in THF; 4.02 ml, 4.02 mmol) was added dropwise and the reaction was stirred at −78° C. for 1 hour. To this was added N-fluorobenzenesulfonimide (1.813 g, 5.75 mmol) as a solution in THF (4 mL). The reaction was stirred at −78° C. for 30 minutes. The reaction was treated with aqueous ammonium chloride solution and extracted with ethyl acetate. The organic portion was e dried over Na2SO4, filtered, concentrated and purified by column chromatography, eluting with 0-40% tert-butyl methyl ether in Heptanes to afford the title compound (1.1 g, 2.01 mmol, 52.4% yield) as a mixture of diastereomers. MS m/z=570.0 (M+Na).

Provenance & Evidence