Hydrochloric Acid → HCID 11169416, compound

Participants

Reaction Steps

2(S)-tert-Butoxycarbonylamino-3(S)-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 (12f) (0.82 g, 1.23 mmol), anisole (0.2 mL) and THF (25 mL) are cooled to 0° C. Hydrogen chloride (4 M in dioxane, 9 mL, 36.8 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-third 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 dried under vacuum to give the title compound in 52% yield (0.39 g). 1H NMR (400 MHz, CD3OD): δ 7.51 (d, 1H), 7.36 (t, 1H), 7.26 (d, 1H), 6.05 (d, 1H), 6.00 (d, 1H), 4.87 (m, 1H), 4.20 (m, 3H), 4.09 (dd, 1H), 3.84 (dd, 1H), 3.37 (m, 2H), 3.23 (tt, 1H), 3.11 (m, 2H), 2.54 (s, 3H), 2.34 (m, 2H), 2.17 (m, 2H), 2.06 (m, 1H), 1.56 (m, 1H), 1.39 (m, 1H), 1.06 (d, 3H), 1.00 (t, 3H). MS-APCI (m/z+): 341, 385, 572.

Provenance & Evidence