Water → HCID 20725640, compound

Participants

Reaction Steps

To a stirred solution of 5(R)-[-N-isoxazol-3-yl-N-(2,2,2-trichloroethyloxycarbonyl)aminomethyl]-3-{3-fluoro-4-[N-(2,2-dimethyl-1,3-dioxolan-4(S)-ylcarbonyl)-1,2,5,6-tetrahydropyrid-4-yl]phenyl}oxazolidin-2-one (200 mg, 0.3 mM) in acetic acid (3 ml) was added zinc dust (195 mg, 3.0 mM). The mixture was stood in an ultrasonic bath for 10 min. then stirred vigorously for 24 hours under a nitrogen atmosphere at ambient temperature. Water (0.5 ml) was added and stirring was continued for a further 24 hours. The reaction mixture was filtered through celite and evaporated. The residue was dissolved in tetrahydrofuran (15 ml)/1.0 M aq. HCl (10 ml) and was stirred at ambient temperature for 3 days. It was evaporated to dryness and the residue was chromatographed by MPLC (8% MeOH/CH2Cl2, gradient to 25%). The title compound was obtained as a white powder on trituration with ether/ethanol (68 mg, 50%). NMR: δ2.42(s, 2H,partially obscured), 3.43(m, 2H), 3.57(m, 1H), 3.79(m, 3H), 4.16(m, 2H), 4.27(m, 1H), 4.38(m, 1H), 4.72(m, 1H), 4.91(m, 1H), 5.00(m, 1H), 6.00(m, 2H), 6.57(t, 1H), 7.30(d of d, 1H), 7.39(t, 1H), 7.50(d of d, 1H), 8.40(s, 1H); m/z ES+(M+H)=447.

Provenance & Evidence