Acetic Acid → 3-(4-(1-(2,2-Dimethyl-1,3-dioxolan-4(S)-ylcarbonyl)-1,2,5,6-tetrahydropyrid-4-yl)-3,5-difluorophenyl)-5(R)-hydroxymethyloxazolidin-2-one

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Reaction Steps

3-(4-(1-(2,2-Dimethyl-1,3-dioxolan-4(S)-ylcarbonyl)-1,2,5,6-tetrahydropyrid-4-yl)-3,5-difluorophenyl)-5(R)-acetoxymethyloxazolidin-2-one (8.64 g, 18 mM) was suspended in methanol (350 ml) and stirred at ambient temperature under nitrogen. Potassium carbonate (3.73 g, 27 mM) was added, and the mixture stirred for 20 minutes only, then neutralised immediately by the addition of acetic acid (2 ml). Saturated aqueous sodium bicarbonate (50 ml) was added, the methanol evaporated, and the residue diluted with water (100 ml) before extraction of the organics into dichloromethane (250 ml+100 ml). The extract was washed with brine (100 ml), dried (magnesium sulfate), evaporated and crude product purified by chromatography on a 300 g silica vacuum sinter column, eluting with a gradient from 0% to 20% methanol in dichloromethane. Relevant fractions were combined to give the desired product (7.3 g). NMR (DMSO-d6) δ: 1.29 (s, 3H); 1.32 (s, 3H); 2.29 (br, 1H); 2.38 (br, 1H); 3.48-3.76 (complex m, 4H); 3.82 (dd, 1H); 4.05 (complex m, 4H); 4.21 (dd, 1H); 4.72 (m, 1H); 4.90 (dd, 1H); 5.22 (t, 1H); 5.86 (s, 1H); 7.35 (d, 2H). MS (ESP): 439 (MH+) for C21H24F2N2O6

Provenance & Evidence