Hydrochloric Acid → HCID 11399515, compound

Participants

Reaction Steps

2(S)-tert-Butoxycarbonylamino-3-phenyl-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 (12 g) (0.78 g, 1.1 mmol), anisole (0.5 mL) and THF (20 mL) are cooled to 0° C. Hydrogen chloride (4 M in dioxane, 8 mL, 33.1 mmol) is added in a dropwise manner. After complete addition, the ice-bath is removed and 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 63% yield (0.45 g). 1H NMR (400 MHz, CD3OD): δ 7.50 (dd, 1H), 7.39-7.24 (m, 7H), 6.02 (d, 1H), 5.97 (d, 1H), 4.86 (m, 1H), 4.50 (dd, 1H), 4.18 (m, 2H), 4.09 (dd, 1H), 3.83 (dd, 1H), 3.35 (m, 3H), 3.21 (m, 2H), 3.11 (m, 2H), 2.53 (s, 3H), 2.34 (m, 2H), 2.16 (m, 2H). MS-APCI (m/z+): 341, 385, 606.

Provenance & Evidence