Hydrochloric Acid → HCID 11215730, compound

Participants

Reaction Conditions

Reaction Steps

2(S)-tert-butoxycarbonylamino-3(S)-methyl-pentanoic acid 1-(acetyl-{3-[4-(1,1-dioxo-hexahydro-1λ6-thiopyran-4-yl)-3-fluoro-phenyl]-2-oxo-oxazolidin-5(R)-ylmethyl}-carbamoyloxy)-ethyl ester (12j) (1.00 g, 1.46 mmol), anisole (0.24 g, 2.188 mmol) and THF (30 mL) are cooled in an ice bath. Hydrochloric acid (4 N in dioxane, 10.94 mL) is added dropwise. The solution is stirred in an ice bath for 30 min and then at RT for 4 h. The reaction mixture is re-cooled to 0° C. and ethyl ether is added. The resulting solids are collected by filtration and washed with a cold ethyl ether/ethyl acetate mixture to afford the title compound. Isolated yield: 64%. 1H NMR (400 MHz, DMSO-d6): δ 8.46 (br s, 3H), 7.43-7.39 (m, 1H), 7.36 (t, 1H), 7.22 (d, 1H), 6.85-6.79 (m, 1H), 4.77-4.71 (m, 1H), 4.13-4.00 (m, 2H), 3.96 (dd, 1H),3.88-3.84 (m, 1H), 3.80-3.74 (m, 1H), 3.51-3.28 (m, partially obscured by water, 2H), 3.18-3.12 (m, 1H), 3.04 (d, 2H), 2.40 (d, 3H), 2.08 (q, 2H), 1.97-1.93 (m, 2H), 1.90-1.84 (br m, 1H), 1.50 (dd, 3H), 1.44-1.36 (m, 1H), 1.26-1.14 (m, 1H), 0.88 (dd, 3H), 0.84-0.79 (m, 3H).

Provenance & Evidence