Sodium Hydroxide → [(4S,5R)-2-Oxo-4,5-diphenyl-1,3-oxazolidin-3-yl]acetic acid

HRID 1762167Notes

Reaction equation

HRID 1762167 reaction equation
[C:1]1([C@H:7]2[C@@H:11]([C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=3)[O:10][C:9](=[O:18])[N:8]2[CH2:19][C:20]([O:22]CC)=[O:21])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[OH-].[Na+]>O1CCCC1.O>[C:1]1([C@H:7]2[C@@H:11]([C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=3)[O:10][C:9](=[O:18])[N:8]2[CH2:19][C:20]([OH:22])=[O:21])[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 674151183-Oxazolidineacetic acid, 2-oxo-4,5-diphenyl-, ethyl ester, cis-

Product 1

HCID 58430307[(4S,5R)-2-Oxo-4,5-diphenyl-1,3-oxazolidin-3-yl]acetic acidYield 78.3%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 8028TetrahydrofuranSolvent

Procedure

Ethyl (4,5-cis-diphenyl-2-oxo-3-oxazolidinyl)acetate (40.6 g, 125 mmol) was dissolved in tetrahydrofuran (100 ml) and a solution of sodium hydroxide (6 g, 150 mmol) in water (40 ml) was added thereto. The mixture was stirred at room temperature for 15 minutes. To the homogeneous solution was added water (150 ml) and the mixture was washed twice with diisopropyl ether (20 ml). The aqueous layer was adjusted to pH 2 with a 10-fold dilution of concentrated hydrochloric acid and extracted with ethyl acetate. The extract was dried over magnesium sulfate and filtered. The filtrate was concentratred and the residue was recrystallized from methylenechloride-n-hexane mixture to give the title compound (29.1 g) as white crystals.

Workup

  1. washthe mixture was washed twice with diisopropyl ether (20 ml)
  2. extractionextracted with ethyl acetate
  3. dry with materialThe extract was dried over magnesium sulfate
  4. filtrationfiltered
  5. customthe residue was recrystallized from methylenechloride-n-hexane mixture

Sources & evidence

ORD record
ord-9d1d13677cfb427a82806909097c676f
Source dataset
uspto-grants-1989_05
Patent number
US04831026

Reaction notes

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