反应详情

To a solution of 4-[(R)-3-(2-methyl-pyridin-4-yl)-3-oxo-1-o-tolyl-propyl]-benzoic acid methyl ester (98 mg) in tetrahydrofuran (3 mL) was added 1 M aq. lithium hydroxide solution (2.62 mL). The reaction mixture was stirred at room temperature for 4 h. A saturated aq. solution of ammonium chloride and ethyl acetate were added, the phases were separated and the inorganic one was extracted with ethyl acetate (2×). The combined organic layers were washed with brine, dried over sodium sulfate, filtered and concentrated in vacuo to yield 4-[(R)-3-(2-methyl-pyridin-4-yl)-3-oxo-1-o-tolyl-propyl]-benzoic acid as a white solid. This was reacted in analogy to example 132, step 6 with hydroxylamine hydrochloride in the presence of sodium hydrogencarbonate to afford the title compound as a white solid (98 mg, 60%), MS (ESI−): m/z=372.9 ([M−H]−).

1. customthe phases were separated
2. extractionthe inorganic one was extracted with ethyl acetate (2×)
3. washThe combined organic layers were washed with brine
4. dry with materialdried over sodium sulfate
5. filtrationfiltered
6. concentrationconcentrated in vacuo