Benzoyl chloride → HCID 86701261, compound

Participants

Reaction Steps

To a solution of (3S,6S,7R,8R)-3-(tert-butoxycarbonylamino)-8-(2-hydroxyethyl)-6 methyl-4,9-dioxo-1,5-dioxonan-7-yl isobutyrate (200 mg, 0.479 mmol) in pyridine (0.5 mL) and CH2Cl2 (1 mL) was added benzoyl chloride (195 mg, 0.958 mmol) at room temperature (about 22° C.), and the reaction mixture was stirred at room temperature for 12 h. The solvents were removed under vacuum and the residue was purified by column chromatography (SiO2, hexanes/EtOAc gradient) to give the title compound (268 mg, 74%) as a white solid: 1H NMR (300 MHz, CDCl3) δ 7.97 (dd, J=8.5, 1.0 Hz, 2H), 7.56-7.40 (m, J=10.6, 3H), 5.39-5.15 (m, 2H), 5.10 (t, J=9.9 Hz, 1H), 4.97-4.73 (m, 2H), 4.42-4.29 (m, 1H), 4.25 (m, 1H), 3.57-3.35 (m, 1H), 2.73 (t, J=9.5 Hz, 1H), 2.62 (dt, J=14.0, 7.0 Hz, 1H), 2.36-2.18 (m, 1H), 1.90-1.71 (m, 1H), 1.46 (s, 9H), 1.28 (d, J=6.4 Hz, 3H), 1.21 (dd, J=7.0, 1.0 Hz, 6H); ESIMS m/z 544 ([M+Na]+).

Provenance & Evidence