Tetrabutylammonium Fluoride → HCID 58997410, compound

Participants

Reaction Conditions

Reaction Steps

Tetrabutylammonium fluoride (6.39 g, 24.48 mmol) is added to a solution of the title A compound, N-(2-trimethylsilylethoxycarbonyl-sulfamoyl)-N-(4-iodo-phenyl)glycine methyl ester (3.15 g, 6.12 mmol) in freshly distilled tetrahydrofuran (60 mL). The reaction is stirred under argon and heated at 90° C. The reaction is monitored by reverse phase HPLC (YMC CombiScreen Pro C18, 50×4.6 mm I.D., particle size S-5 micron, 12 nM) eluting at 3 mL/min with a gradient of 90:10 (0.1% TFA in water: MeCN) to 10:90 at 7.0 min. Starting material has a retention time of 4.88 min and the product has a retention time of 2.83 min. After 24 h, the reaction is poured into 500 mL of 1N aqueous HCl and extracted with EtOAc. The organic solution is treated with Na2SO4 and charcoal, filtered through celite and concentrated to give an oil. Crystallization from EtOAc/hexane (and some additional charcoal) yields 5-(4-iodo-phenyl)-1,1-dioxo-1,2,5-thiadiazolidin-3-one as a light yellow powder: mp=191-193° C., [M−H]−=336.8.

Provenance & Evidence