Sulfuric Acid → 5-(1-Hydroxy-1-methylethyl)-2-[(phenylmethyl)oxy]-N-3-pyridinylbenzamide

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Reaction Steps

3M Methylmagnesium bromide (0.10 ml, 0.29 mmol) was added to a solution of 5-acetyl-2-[(phenylmethyl)oxy]-N-3-pyridinylbenzamide (may be prepared as described in Example 72; 100 mg, 0.29 mmol) in tetrahydrofuran (3 ml) at 0° C. The solution was stirred for 45 minutes. Another 3 equivalents of 3M methylmagnesium bromide (300 ul) were added at 0° C. and solution was stirred for 18 hours. 1N H2SO4 (5 ml) was then added, the mixture was stirred for 3 minutes, then ethyl acetate (10 ml) was added. The acid layer was basified to pH 9 using saturated NaHCO3 solution. The organic layer was washed with saturated NaHCO3 solution (5 ml), dried (MgSO4) and the solvent was removed in vacuo. The residue was purified by MDAP to give the title compound as a white solid. 61 mg.

Provenance & Evidence