Potassium Iodide → HCID 23132881, compound

Participants

Reaction Steps

0.45 g of the Wang-resin-bound 2-[(1-hydroxy-naphthalene-2-carbonyl)-amino]-2-methyl-propionic acid (loading 0.35 mmol/g) was placed in a reaction vessel with 3 ml of dimethylformamide. To this was added 0.058 g of 2-chloromethyl-1H-benzoimidazole, 0.228 g of cesium carbonate and 0.023 g of potassium iodide. The reaction was then placed in a vortex shaker overnight. The resin was filtered, washed four times each with dimethylformamide, methanol and dichloromethane. To this was added a solution of 30% trifluoroacetic acid, 65% dichloromethane and 5% triethylsilane and left in vortex shaker for 1.5 hours. The resin was filtered and the filtrate concentrated in vacuo. Purification by flash chromatography on silica with dichloromethane/methanol afforded 25 mg of 2-{[1-(1H-Benzoimidazol-2-ylmethoxy) naphthalene-2-carbonyl]-amino}-2-methyl-propionic acid.

Provenance & Evidence