Sodium Thiosulfate → HCID 178456080, compound

Participants

Reaction Steps

(S)-[1-(Benzoxazol-2-yl-hydroxy-methyl)-propyl]-amide hydrochloride (90 mg, 0.254 mmol), 3-iminoisoindolinone (100 mg, 0.684 mmol), and N,N-diisopropylethyl-amine (0.2 mL) were dissolved in THF (10 mL) and heated at reflux for 5 h. After dilution with ethyl acetate (150 mL), the solution was washed with saturated aqueous NaHCO3 solution and brine, dried with MgSO4 and evaporated under vacuum. The crude product was dissolved in dry dichloromethane (10 mL) and Dess-Martin Periodinane (400 mg, 0.96 mmol) was added. After stirring at ambient temperature for 1 h, the reaction mixture was diluted with ethyl acetate (150 mL) and treated with 0.26 M Na2S2O3 solution in saturated aqueous NaHCO3. The organic phase was washed with saturated aqueous NaHCO3 and brine, dried with MgSO4 and evaporated. The product was purified by flash chromatography on silica gel (hexane/ethyl acetate 2:1) to yield the title compound (20 mg; 0.045 mmol) as a 1:1 mixture of isomers.

Provenance & Evidence