Azide → HCID 59485944, compound

Participants

Reaction Steps

(4S,5R)-3-(4-chlorophenyl)-4-(3-(trifluoromethyl)phenyl)-5-(hydroxymethyl)oxazolidin-2-one (from Example 72) was converted into (4S,5S)-5-(azidomethyl)-3-(4-chlorophenyl)-4-(3-(trifluoromethyl)phenyl)oxazolidin-2-one as described in Example 34. The azide (0.076 mmol) was then dissolved in t-butanol:water (2:1, 0.5 mL) and treated with 3-fluorophenylacetylene (0.076 mmol), followed by copper (II) sulfate pentahydrate (0.4 mg) and sodium ascorbate (0.75 mg). After stirring for 2 h, the reaction mixture was quenched with water and extracted with ethyl acetate, dried over magnesium sulfate, filtered and concentrated. Purification on silica gel (30% ethyl acetate/hexanes) gave the title compound as a colorless oil. 1H NMR (acetone-d6) δ (ppm) 8.57 (s, 1H), 7.88 (s, 1H), 7.79 (d, J=7.7 Hz, 1H), 7.72-7.70 (m, 2H), 7.67-7.63 (m, 2H), 7.50-7.44 (m, 3H), 7.30-7.28 (m, 2H), 7.11 (td, J=8.5, 2.3 Hz, 1H), 5.81 (d, J=5.2 Hz, 1H), 5.22-5.16 (m, 2H), 5.07 (ddd, J=5.5, 5.5, 4.4 Hz, 1H), 4.73-4.64 (m, 3H), 4.01 (d, J=3.6 Hz, 2H); HPLC-MS calculated C25H17ClF4N4O2 (M+H+): 517.1, found: 517.1.

Provenance & Evidence