Triphenylphosphine → tert-Butyl 3-((4-((S)-3-((S)-4-benzyl-2-oxooxazolidin-3-yl)-1-(isoxazol-3-yl)-3-oxopropyl)phenoxy)methyl)phenylcarbamate

Participants

Reaction Steps

To a solution of alcohol 27.1 (179 mg, 0.765 mmol) in THF (7 mL), was added phenol 7.5 (300 mg, 0.765 mmol), DIAD (0.155 mL, 0.803 mmol), and triphenylphosphine (211 mg, 0.803 mmol). The solution was stirred for 16 hours and then concentrated to a reduced volume. The residue was purified by medium pressure chromatography (silica gel, 0 to 50% EtOAc:hexanes) to give 27.2 (440 mg). MS ESI (pos.) m/e 598.2 (M+H). 1H NMR (400 MHz, CDCl3) δ ppm 8.20 (1 H, d, J=1.6 Hz), 7.38 (1 H, s), 7.08-7.29 (8 H, m), 7.00 (1 H, d), 6.82 (2 H, d, J=8.6 Hz), 6.54 (1 H, s), 6.33 (1 H, br. s.), 6.05 (1 H, d, J=1.6 Hz), 4.92 (2 H, s), 4.85-4.90 (1 H, m), 4.66 (1 H, dd, J=1.6 Hz), 4.49-4.58 (1 H, m), 4.01-4.04 (1 H, m), 3.93 (1 H, dd, J=17.6, 8.2 Hz), 3.45 (1 H, dd, J=17.6, 6.7 Hz), 3.11 (1 H, dd, J=13.5, 3.3 Hz), 2.68 (1 H, dd, J=13.3, 9.4 Hz), 1.43 (9 H, s).

Provenance & Evidence