(S)-N-((3-(3-fluoro-4-Morpholinophenyl)-2-oxooxazolidin-5-yl)Methyl)ethanethioaMide → HCID 53751722, compound

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Reaction Steps

A stirred mixture of 6 (0.38 g, 0.00118 mol) in dioxane (20 mL), under nitrogen was treated with 4 (0.51 g, 0.00126 mol), warmed to reflux during 30 min and kept at this temperature for 90 min. It was then evaporated under a stream of nitrogen. The residue was chromatographed on silica gel with 1.25% MeOH—CH2Cl2 and the slightly impure product was rechromatographed on silica gel with 25% EtOAc-CH2Cl2. The resulting product was crystallized from EtOAc-methyl tert-butyl ether to give 0.114 g of 7: mp 150-155° C. (dec.); IR (DRIFT) 3322, 1752 cm−1; MS(ES) m/z 340 (M+H+), 362 (M+Na+); 1HNMR [300 MHz, (CD3)2SO] d 2.94 (m, 4H), 3.72 (m, 4H), 3.77 (d,d, 1H), 3.94 (t, 2H), 4,12 (t, 1H), 4.93 (m, 1H), 7.05 (t, 1), 7.16 (d,d, 1H), 7.47 (d,d, 1H), 9.33 (d, 1H), 10.59 (s, 1H), Anal. cald for C15H18FN3O3S: C, 53.08; H, 5,35; N, 12.38. Found: C, 53.02; H, 5.44; N, 12.36.

Provenance & Evidence