Hydrochloric Acid → (S)-4-(5,5-dimethyl-2-oxo-4-phenyloxazolidin-3-yl)benzoic acid

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Reaction Conditions

Reaction Steps

To a flask charged with (S)-methyl 4-(5,5-dimethyl-2-oxo-4-phenyloxazolidin-3-yl)benzoate (2.70 g, 8.30 mmol) were added THF (48.5 mL), MeOH (48.5 mL) and water (48.5 mL) respectively. To the resulting turbid solution was added LiOH (0.994 g, 41.5 mmol), and the resulting mixture was heated at 50° C. overnight. The resulting mixture was cooled in an ice water bath and brought to pH˜2 by the addition of 2N HCl (˜15 mL) leading to a light yellow solution to which water was added (˜100 mL). This lead to the formation of a white precipitate which was collected by vacuum filtration and washed with excess water. After drying under high vacuum overnight, (S)-4-(5,5-dimethyl-2-oxo-4-phenyloxazolidin-3-yl)benzoic acid (1.25 g, 4.02 mmol, 48.4% yield) was obtained as a white solid. NMR indicated that the product formed as a THF adduct with a 3:2 product to THF ratio. 1H NMR (400 MHz, DMSO-d6) δ=12.76 (br. s., 1H), 7.87-7.81 (m, 2H), 7.63-7.57 (m, 2H), 7.41-7.34 (m, 2H), 7.34-7.30 (m, 1H), 7.30-7.19 (m, 2H), 5.51 (s, 1H), 1.63 (s, 3H), 0.91 (s, 3H).

Provenance & Evidence