Tetrabutylammonium Fluoride → HCID 67138424, compound

Participants

Reaction Conditions

Reaction Steps

A solution of tetrabutylammonium fluoride (5.88 g, 18.67 mmol) in THF (40 mL) is added a solution of the title A compound, N-(2-trimethylsilylethoxycarbonyl-sulfamoyl)-N-(3-iodo-phenyl)glycine methyl ester (2.33 g, 4.5 mmol) in THF (50 mL). The reaction is heated at 90° C. and 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 4.82 min and the product has a retention time of 2.81 min. After 24 h, the reaction is poured into 500 mL of 1N aqueous HCl and extracted with EtOAc. The organic solution is dried over anhydrous MgSO4, filtered and concentrated to give a yellow solid. Trituration with EtOAc/hexane yields 5-(3-iodo-phenyl)-1,1-dioxo-1,2,5-thiadiazolidin-3-one as a white solid: (M−H)−=336.9.

Provenance & Evidence