Water → HCID 58599399, compound

Participants

Reaction Conditions

Reaction Steps

Thioacetic acid S-{2-oxo-2-[4-(4-trifluoromethoxy-benzenesulfonylamino)-phenyl]-ethyl}ester (SI-4) (0.5 g, 1.15 mmol) was dissolved in anhydrous DMF (5 ml). Lithium hydroxide (28 mg, 1.15 mmol) was added and the solution was sonicated until homogeneous and heated to 90° C. for 4 hours. The solution was allowed to cool to room temperature and valeryl chloride (150 mg, 1.27 mmol) was added and the mixture stirred for 16 hours. The solution was partioned between 20 ml each water and EtOAc. The organic layer was washed with water, then brine and dried over Na2SO4. The solution was then filtered, stripped of solevent and the product purified by flash chromatography (100% DCM). The solvent was evaporated to afford 107 mg (0.22 mmol, 19%) product as a clear oil. 1H-NMR: (400 MHz, DMSO): 8.07 (d, 2H), 7.60 (d, 2H), 7.40 (d, 2H), 7.25 (d, 2H), 2.40 (s, 2H), 2.10 (t, 2H), 1.42 (t, 2H) 1.11 (t,2H), 0.09 (t, 3H); LC-MS (ES+): 476 [M]+ m/e.

Provenance & Evidence