Ethylene Glycol → 2-Hydroxyethyl 4-chloro-2-((2-furylmethyl)amino)-5-sulfamoylbenzoate

Beteiligte Stoffe

Reaktionsschritte

To a solution of furosemide (OnBio, Canada, 5.2 g, 15.6 mmol) in a mixture of CH2Cl2/DMF (15 mL /20 mL) was added ethylene glycol (Aldrich, Wis., U.S., 4.4 mL, 78.0 mmol) and DMAP (377.5 mg, 3.1 mmol). A solid formed upon the addition of the DMAP and additional DMF (15 mL) was added followed by EDAC (3.9 g, 20.3 mmol). The reaction mixture was allowed to stir at room temperature for 24 hours. The solvent was removed under reduced pressure and the residue redissolved in CH2Cl2 (100 mL). The sample was washed with H2O (3×50 mL), brine, and the sample dried (MgSO4). The residue after evaporation was chromatographed on silica gel eluting with 1:1 hexanes/EtOAc to give the title compound (1.4 g, 24% yield) as a white solid. 1H NMR (300 MHz, CDCl3) δ 8.45-8.43 (m, 2H), 7.64 (s, 1H), 7.35 (s, 2H), 7.09 (s, 1H), 6.42-6.41 (m, 1H), 6.37-6.36 (m, 1H), 4.92 (t, J=5.4 Hz, 1H), 4.60 (d, J=5.8 Hz, 2H), 4.28 (br t, 2H), 3.71-3.65 (m, 2H). Mass Spectrum (API-TIS) m/z 375 (MH+).

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