Trimethylsilyl iodide → HCID 86762223, compound

Participants

Reaction Steps

A solution of benzyl(4aR,7aR)-2-benzamido-7a-(2-thienyl)-4,4a,5,7-tetrahydropyrrolo[3,4-d][1,3]thiazine-6-carboxylate (14 g, 29.3 mmol) in acetonitrile (210 mL) is treated with iodotrimethylsilane (7.53 mL, 52.7 mmol) at room temperature. The solution is stirred for 1 hour and the solvent is evaporated. The residue is quenched with 1 M hydrochloric acid and ethyl acetate and the resulting mixture is filtered through diatomaceous earth. The aqueous layer is separated, neutralized with 50% w/w aqueous solution of sodium hydroxide and extracted with ethyl acetate. The organic extracts are dried over sodium sulfate and concentrated to give the title compound (7.9 g, 78%). ES/MS (m/e): 344 (M+H).

Provenance & Evidence