Potassium Hydroxide → 2-[(Tert-butoxycarbonyl-{4-[2-(5-methyl-2-phenyl-oxazol-4-yl)-ethoxy]-phenyl}-amino)-methyl]-benzoic acid ethyl ester

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Reaction Steps

To a suspension of 3.41 g of powdered KOH in 110 ml of DMSO was added at 22° C. 6.00 g of {4-[2-(5-methyl-2-phenyl-oxazol-4-yl)-ethoxy]-phenyl}-carbamic acid tert-butyl ester and the suspension was stirred for 25 min. A solution of 7.40 g of 2-bromomethyl-benzoic acid ethyl ester in 10 ml of DMSO was added slowly keeping the temperature at 15-20° C. and stirring was continued at 22° C. for 2.5 h. The dark mixture was partitioned between 500 ml of a saturated aqueous NH4Cl and 200 ml of AcOEt, the organic layer was washed with saturated aqueous NH4Cl and water, dried and evaporated. The residue was purified by chromatography (SiO2, n-hexane/AcOEt 4:1) to give 7.96 g of the title compound as a pale yellow oil. MS: (M+H)+ 557.3.

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