Sodium Thiosulfate → HCID 178457877, compound

Participants

Reaction Steps

To a stirred solution of N-[1-(benzoxazol-2-yl-hydroxymethyl)propyl]-3-cyclohexyl-2-[(methanesulfonyliminophenylmethyl)amino]propionamide (250 mg, 0.463 mmol) in dry THF (10 mL) was added at room temperature Dess-Martin periodinane (265 mg, 0.626 mmol), and the mixture was stirred at the same temperature for 1 h. A 25% sodium thiosulfate solution (3 mL) and saturated sodium bicarbonate solution (3 mL) were added. The biphasic mixture was stirred for additional 30 min, diluted with ethyl acetate (30 mL), and washed with brine and then water. The organic extracts were were dried, concentrated in vacuo, and purified by flash chromatography on silica gel (eluted with 1:1 EtOAc/hexanes) to yield 188 mg (75%) of the title compound as a mixture of E/Z isomers in ca. 3.5:1 ratio. 1H NMR for a major isomer (400 MHz, CDCl3): δ 7.97–7.40 (9H, m), 6.96(1H, d, J=8.0 Hz), 6.11(1H, d, J=7.6 Hz), 5.71(1H, m), 4.81(1H, m), 3.07(s, 3H), 2.35–0.80(m, 15H), 1.13(3H, t, J=7.2 Hz). MS: 539.3(MH+).

Provenance & Evidence