Water → HCID 20815203, compound

Participants

Reaction Conditions

Reaction Steps

380 mg (1.19 mmol) of 2-(4-bromobutyl)-1,1-dioxo-1,2-dihydro-1λ6-benzo[d]isothiazol-3-one and 263 μl (1.51 mmol) of N-ethyldiisopropylamine are added to a solution of 224 mg (0.58 mmol) of benzyl-[4-(tert-butyldimethylsilanyloxy)chroman-2-ylmethyl]amine in 1.25 ml of dry N-methylpyrrolidinone. The reaction mixture is stirred at 120° C. for 3 hours. After cooling to room temperature, 2 ml of water are added, resulting in the precipitation of a dark, viscous product. The supernatant is decanted and the residue is washed twice with in each case 1.5 ml of water. The product is then dissolved in 3 ml of dichloromethane, the residue water is removed by drying and the solution is evaporated to dryness. The crude product is purified by HPLC chromatography under the following conditions: column Nucleosil® 100 C-18, 125×16 mm (particle size 7 μm), column temperature room temperature, mobile phase 85% acetonitrile/15% water (v/v), flow rate 6 ml/min, UV detection at 230 nm. The product-containing fractions are combined and evaporated to dryness. The residue is dissolved in 2.5 ml of ethanol and 6 ml of acetone and again evaporated to dryness. The product is dried in a desiccator over blue gel.

Provenance & Evidence