Lithium Hydroxide → 3-(2-Oxo-1,3-oxazolidin-3-yl)benzoic acid

HRID 1612442Notes

Reaction equation

HRID 1612442 reaction equation
C[O:2][C:3](=[O:16])[C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([N:10]2[CH2:14][CH2:13][O:12][C:11]2=[O:15])[CH:5]=1.[Li+].[OH-]>O1CCOCC1>[O:15]=[C:11]1[N:10]([C:6]2[CH:5]=[C:4]([CH:9]=[CH:8][CH:7]=2)[C:3]([OH:16])=[O:2])[CH2:14][CH2:13][O:12]1

Participants

4

Reactant 2

HCID 3939Lithium HydroxideHCID 695897133-(2-Oxooxazolidin-3-yl)benzoic Acid Methyl Ester

Product 1

HCID 222530423-(2-Oxo-1,3-oxazolidin-3-yl)benzoic acidYield 60%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

3-(2-Oxooxazolidin-3-yl)benzoic acid methyl ester (D118) (110 mg, 0.5 mmol) in dioxane (2.5 ml) was treated with 1M LiOH solution (0.75 ml) and the mixture was stirred at room temperature for 1.5 h. Amberlyst 15 was then added and stirring continued for 15 mins. The resin was filtered and the filtrate evaporated to dryness. Th residue was tritutated with diethyl ether to afford the title compound (62 mg, 60%).

Workup

  1. additionAmberlyst 15 was then added
  2. stirringstirring
  3. waitcontinued for 15 mins
  4. filtrationThe resin was filtered
  5. customthe filtrate evaporated to dryness

Sources & evidence

ORD record
ord-e46ad5cceda64c598328ea23b390abf7
Source dataset
uspto-grants-2006_01
Patent number
US06992103B2

Reaction notes

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