Hydrochloric Acid → (R)-piperidine-4-carboxylic acid (acetyl-{3-[4-(1,1-dioxo-hexahydro-1lambda6-thiopyran-4-yl)-3-fluoro-phenyl]-2-oxo-oxazolidin-5-ylmethyl}-carbamoyloxy)-methyl ester hydrochloride

Participants

Reaction Steps

(R)-Piperidine-1,4-dicarboxylic acid 4-[(acetyl-{3-[4-(1,1-dioxo-hexahydro-1λ6-thiopyran-4-yl)-3-fluoro-phenyl]-2-oxo-oxazolidin-5-ylmethyl}-carbamoyloxy)-methyl] ester 1-tert-butyl ester (17) (588.5 mg, 0.88 mmol) and anisole (0.9 mL) are diluted with tetrahydrofuran (17 mL). Hydrochloric acid in dioxane (4 M, 6.6 mL) is added dropwise and the resultant mixture is stirred at RT overnight. Ether is 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 quantitative yield (530.8 mg, 0.88 mmol) 1H NMR (400 MHz, CD3OD): δ 7.51 (dd, 1H), 7.36 (t, 1H), 7.26 (dd, 1H), 5.92 (s, 2H), 4.15-422 (m, 2H), 4.05 (dd, 1H), 3.81 (dd, 1H), 3.36-3.43 (m, 4H), 3.23 (tt, 1H), 3.05-3.14 (m, 5H), 2.90 (tt, 1H), 2.52 (s, 3H), 2.35 (q, 2H), 2.13-2.26 (m, 4H), 1.92-2.00 (m, 2H). MS-APCI (m/z+): 570.

Provenance & Evidence