Hydrochloric Acid → 3-(4-(3(S)-Aminopyrrolidin-1-yl)-3-fluorophenyl)-5(R)-(N-(2,2,2-trichloro-ethyloxycarbonyl)isoxazol-3-ylaminomethyl)oxazolidin-2-one

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Reaction Steps

3-(4-(3(S)-(t-Butoxycarbonyl)aminopyrrolidin-1-yl)-3-fluorophenyl)-5(R)-(N-(2,2,2-trichloroethyloxycarbonyl)isoxazol-3-ylaminomethyl)oxazolidin-2-one (1.03 g, 1.62 mM) was dissolved in dichloromethane (5 ml) under nitrogen and treated with a solution of hydrogen chloride in ethanol (3.8 M, 25 ml). After stirring 5 hours at ambient temperature, solvent was removed, and the residue evaporated repeatedly with portions of dichloromethane to give the hydrochloride salt of the desired product as a white foam (962 mg ). NMR (DMSO-d6) δ: 2.02 (hextet, 1H); 2.25 (hextet, 1H); 3.26 (dd, 1H); 3.42 (m overlapped by solvent, ˜1H); 3.53 (m, 2H); 3.84 (dd overlapping m, 2H); 4.15 (m, 2H); 4.35 (dd, 1H); 4.97 (d, 1H); 5.02 (m, 1H); 5.08 (d, 1H); 6.77 (t, 1H); 6.88 (d, 1H); 7.12 (dd, 1H); 7.39 (dd, 1H); 8.48 (br, 3H); 8.91 (d, 1H). (+1 proton for HCl salt). MS (ESP): 536 (MH+) for C20H21Cl3FN5O5

Provenance & Evidence