Hydrochloric Acid → HCID 11203843, compound

Participants

Reaction Steps

To a mixture of the 2(S)-tert-butoxycarbonylamino-propionic acid (acetyl-{3-[4-(1,1-dioxo-hexahydro-1λ6-thiopyran-4-yl)-3-fluoro-phenyl]-2-oxo-oxazolidin-5(R)-ylmethyl}-carbamoyloxy)-methyl ester (12b) (0.98 g, 1.56 mmol), anisole (1 mL) and THF (30 mL), is added hydrogen chloride (4 M in dioxane, 11 mL, 46.8 mmol) in a dropwise manner. The mixture is stirred at RT overnight. Under reduced pressure, the mixture is concentrated to one-half of its original volume. Ether is then added dropwise to the mixture while stirring, 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 38% yield (0.34 g). 1H NMR (400 MHz, CD3OD): δ 7.51 (dd, 1H), 7.37 (t, 1H), 7.26 (dd, 1H), 6.02 (ABq, 2H), 4.87 (m, 1H), 4.29 (app q, 1H), 4.19 (m, 2H), 4.10 (dd, 1H), 3.83 (dd, 1H), 3.37 (m, 2H), 3.23 (tt, 1H),3.12 (m, 2H), 2.54 (s, 3H), 2.35 (m, 2H), 2.18 (m, 2H), 1.59 (d, 3H). MS-APCI (m/z+): 530.

Provenance & Evidence