Trifluoroacetic acid → (3S)-3-(4-Chlorobenzyl)-4-((4R,5S)-4-methyl-2-oxo-5-phenyl-oxazolidin-3-yl)-4-oxo-butyric acid

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Reaction Steps

A solution of (3S)-3-(4-Chlorobenzyl)-4-((4R,5S)-4-methyl-2-oxo-5-phenyl-oxazolidin-3-yl)-4-oxo-butyric acid tert-butyl ester (5.1 g, 11 mmol) in DCM (100 mL) was treated with TFA (50 mL) and stirred at room temperature for 1 hour. The solution was concentrated in vacuo, taken up into toluene and then conc. in vacuo. Placed on high vacuum for 6 hours to give (3S)-3-(4-Chlorobenzyl)-4-((4R,5S)-4-methyl-2-oxo-5-phenyl-oxazolidin-3-yl)-4-oxo-butyric acid (4.5 g, 100%.) 1H NMR (CDCl3, 400 MHz) δ 7.44-7.37 (3H, m), 7.31-7.21 (6H, m), 5.48 (1H, d, J 6.9 Hz), 4.70-4.63 (1H, m), 4.50-4.42 (1H, m), 3.05 (1H, dd, J 13.3 and 6.2 Hz), 2.89 (1H, dd, J 17.7 and 10.6 Hz), 2.63 (1H, dd, J 13.2 and 9.0 Hz), 2.43 (1H, dd, J 17.6 and 4.4 Hz), 0.86 (3H, d, J 6.6 Hz.)

Provenance & Evidence