Potassium Carbonate → 2-[4-(2-oxo-1,3-Oxazolidin-3-yl)phenyl]propanoic Acid

HRID 1282020

Reaction equation

HRID 1282020 reaction equation
Cl[CH2:2][CH2:3][O:4][C:5]([NH:7][C:8]1[CH:13]=[CH:12][C:11]([CH:14]([CH3:18])[C:15]([OH:17])=[O:16])=[CH:10][CH:9]=1)=[O:6].C(=O)([O-])[O-].[K+].[K+].C(OC(=O)C)C.C(OC(C)C)(C)C>CN(C)C=O>[O:6]=[C:5]1[N:7]([C:8]2[CH:13]=[CH:12][C:11]([CH:14]([CH3:18])[C:15]([OH:17])=[O:16])=[CH:10][CH:9]=2)[CH2:2][CH2:3][O:4]1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 184235752-(4-{[(2-Chloroethoxy)carbonyl]amino}phenyl)propanoic AcidHCID 22281796Diisopropylether ethyl acetate

Product 1

HCID 120432422-[4-(2-oxo-1,3-Oxazolidin-3-yl)phenyl]propanoic AcidYield 80.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

0.5 g (1.85 mmol) of 2-(4-{[(2-chloroethoxy)carbonyl]amino}phenyl)propanoic acid were dissolved in 10 ml of N,N-dimethylformamide and 0.45 g (3.7 mmol) of potassium carbonate were added. After 48 hours the solvent was evaporated under vacuum, the residue redissolved with dichloromethane and washed with hydrochloric acid 0.5 N. The organic layer was dried over sodium sulphate and evaporated. 0.35 g (80% yield) of the title compound crystallized from a mixture ethylacetate-diisopropylether.

Workup

  1. customAfter 48 hours the solvent was evaporated under vacuum
  2. dissolutionthe residue redissolved with dichloromethane
  3. washwashed with hydrochloric acid 0.5 N
  4. dry with materialThe organic layer was dried over sodium sulphate
  5. customevaporated

Sources & evidence

ORD record
ord-4e45ff92dcff41428fe741d375b28032
Source dataset
uspto-grants-2002_09
Patent number
US06455559B1

Linked notes

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