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

HRID 525319Notes

Reaction equation

HRID 525319 reaction equation
[CH3:1][C:2]1([CH3:24])[O:6][C:5](=[O:7])[N:4]([C:8]2[CH:17]=[CH:16][C:11]([C:12]([O:14]C)=[O:13])=[CH:10][CH:9]=2)[C@H:3]1[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1.C1COCC1.[Li+].[OH-].Cl>O.CO>[CH3:1][C:2]1([CH3:24])[O:6][C:5](=[O:7])[N:4]([C:8]2[CH:17]=[CH:16][C:11]([C:12]([OH:14])=[O:13])=[CH:10][CH:9]=2)[C@H:3]1[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 8028TetrahydrofuranHCID 71680861(S)-methyl 4-(5,5-dimethyl-2-oxo-4-phenyloxazolidin-3-yl)benzoate

Product 1

HCID 71681650(S)-4-(5,5-dimethyl-2-oxo-4-phenyloxazolidin-3-yl)benzoic acidYield 48.4%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent2×

Conditions

Temperature
50 °C

Procedure

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).

Workup

  1. temperatureThe resulting mixture was cooled in an ice water bath
  2. additionwas added (˜100 mL)
  3. filtrationThis lead to the formation of a white precipitate which was collected by vacuum filtration
  4. washwashed with excess water
  5. customAfter drying under high vacuum overnight

Sources & evidence

ORD record
ord-d74509128fd34f99b592ec7a8f545428
Source dataset
uspto-grants-2016_05
Patent number
US09340549B2

Reaction notes

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