Hydrochloric Acid → HCID 11307987, compound

Participants

Reaction Steps

To a mixture of 2(S)-tert-Butoxycarbonylamino-4-methyl-pentanoic acid (acetyl-{3-[4-(1,1-dioxo-hexahydro-1λ6-thiopyran-4-yl)-3-fluoro-phenyl]-2-oxo-oxazolidin-5(R)-ylmethyl}-carbamoyloxy)-methyl ester (12e) (0.35 g, 0.52 mmol), anisole (0.5 mL) and THF (10 mL), is added hydrogen chloride (4 M in dioxane, 4 mL, 15.7 mmol) in a dropwise manner. The mixture is stirred at RT overnight. Ether is then added dropwise to the mixture while stirring. Under reduced pressure, the mixture is concentrated to one-third of its original volume. Ether is again added, resulting in the formation of a solid. The solid is collected via filtration, rinsed with ether and ethyl acetate, and dried under vacuum to give the title compound in 39% yield (0.12 g). 1H NMR (400 MHz, CD3OD): δ 7.52 (dd, 1H), 7.37 (t, 1H), 7.26 (dd, 1H), 6.02 (ABq, 2H), 4.88 (m, 1H), 4.20 (m, 3H), 4.10 (dd, 1H), 3.83 (m, 1H), 3.35 (m, 2H), 3.23 (tt, 1H), 3.12 (m, 2H), 2.54 (s, 3H), 2.35 (m, 2H), 2.17 (m, 2H), 1.85 (m, 2H), 1.72 (m, 1H), 1.02 (d, 3H), 1.01 (d, 3H). MS-APCI (m/z+): 341, 385, 572.

Provenance & Evidence