(Oxan-4-yl)methanol → methyl 5-(N-(2,4-dimethylphenyl)-N-isobutylsulfamoyl)-2-((tetrahydro-2H-pyran-4-yl)methoxy)benzoate

Participants

Reaction Conditions

Reaction Steps

To a solution of methyl 5-(N-(2,4-dimethylphenyl)-N-isobutylsulfamoyl)-2-hydroxybenzoate (100 mg, 0.255 mmol) and (tetrahydro-2H-pyran-4-yl)methanol (29.7 mg, 0.255 mmol) in toluene (1.5 mL) stirred in air at room temperature was added a solution of 2-(tributylphosphoranylidene)acetonitrile (61.7 mg, 0.255 mmol) in toluene (0.5 mL). The reaction mixture was then stirred at 20° C. for 24 hours. After this time, additional 2-(tributylphosphoranylidene)acetonitrile (61.7 mg, 0.255 mmol) was added and the reaction stirred for a further 2 hours. The solvent was evaporated and the purification attempted by mass directed autoprep (ammonium carbonate modifier). The relevant fractions were concentrated under a stream of nitrogen to give a mixture of two products. Further purification was carried out by mass directed autoprep (Method O), to provide the desired product, 25 mg. LCMS [LCMS2] Rt 1.44 min, m/z (ES+) 490 (M+H).

Provenance & Evidence