Hydrochloric Acid → HCID 89813479, compound

HRID 525408Notes

Reaction equation

HRID 525408 reaction equation
[OH-].[Li+].[CH3:3][C:4]1([CH3:27])[O:8][C:7](=[O:9])[N:6]([C:10]2[CH:19]=[CH:18][C:13]([C:14]([O:16]C)=[O:15])=[C:12]([CH3:20])[CH:11]=2)[C@H:5]1[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1.O.Cl>C1COCC1.CO>[CH3:3][C:4]1([CH3:27])[O:8][C:7](=[O:9])[N:6]([C:10]2[CH:19]=[CH:18][C:13]([C:14]([OH:16])=[O:15])=[C:12]([CH3:20])[CH:11]=2)[C@H:5]1[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 962Water2×HCID 3939Lithium HydroxideHCID 89814001HCID 89814001, compound

Product 1

HCID 89813479HCID 89813479, compoundYield 92%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
50 °C

Procedure

Lithium hydroxide (0.053 g, 2.210 mmol) was added to a solution of (S)-methyl 4-(5,5-dimethyl-2-oxo-4-phenyloxazolidin-3-yl)-2-methylbenzoate (0.150 g, 0.442 mmol) in THF (2.5 mL), MeOH (2.50 mL), and water (2.50 mL). The mixture was heated at 50° C. for 16 hours. The reaction mixture was then cooled in an ice bath and adjusted to pH˜2 by the addition of 1 N aqueous HCl solution. Water was added, leading to the formation of a white precipitate. The precipitated material was filtered away and dried to afford (S)-4-(5,5-dimethyl-2-oxo-4-phenyloxazolidin-3-yl)-2-methylbenzoic acid (0.132 g, 0.406 mmol, 92% yield) as a white solid. 1H NMR (400 MHz, DMSO-d6) δ ppm 0.91 (s, 3H), 1.63 (s, 3H), 2.44 (s, 3H), 5.51 (s, 1H), 7.18-7.44 (m, 6H), 7.48 (d, J=2.15 Hz, 1H), 7.75 (d, J=8.70 Hz, 1H), 12.57 (br. s., 1H). m/z (ESI) 326 (M+H)+.

Workup

  1. temperatureThe reaction mixture was then cooled in an ice bath
  2. filtrationThe precipitated material was filtered away
  3. customdried

Sources & evidence

ORD record
ord-5ea0f5da6d7643d5a331c139c6f2a403
Source dataset
uspto-grants-2016_05
Patent number
US09340549B2

Reaction notes

Loading…