Isocyanate → 5-(2-Benzyloxy-4-iodophenyl)-1,1-dioxo-1,2,5-thiadiazolidin-3-one

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Reaction Steps

Tetrabutylammonium fluoride (1.0M in THF, 15 mL) is added to a solution of PS-isocyanate resin (3.5 g) in THF. The mixture is stirred at RT for 2 h. The resin is filtered off and the filtrate is added to a solution of 5-(2-benzyloxy-4-iodophenyl)-1,1-dioxo-2-(2-trimethylsilanylethyl)-1,2,5-thiadiazolidin-3-one (5.0 g, 9.18 mmol) in THF. The reaction is stirred at 50° C. for 18 h. The mixture is cooled and concentrated. The residue is partitioned between EtOAc and water and the organic layer is washed with 1N HCl (5×50 mL) and brine. The organic layer is dried over Na2SO4 and concentrated. The residue is purified by reverse phase chromatography using a 10-60% gradient of EtOH/water as eluent to afford the title compound as a light yellow solid: (M−1)−=442.

Provenance & Evidence