Water → 2-{4-[Hydroxy(2-oxothiolan-3-yl)methyl]phenyl}propionic acid

HRID 1685814Notes

Reaction equation

HRID 1685814 reaction equation
[OH:1][CH:2]([CH:16]1[CH2:20][CH2:19][S:18][C:17]1=[O:21])[C:3]1[CH:8]=[CH:7][C:6]([CH:9]([CH3:15])[C:10]([O:12]CC)=[O:11])=[CH:5][CH:4]=1.S(=O)(=O)(O)O.O>O1CCOCC1>[OH:1][CH:2]([CH:16]1[CH2:20][CH2:19][S:18][C:17]1=[O:21])[C:3]1[CH:8]=[CH:7][C:6]([CH:9]([CH3:15])[C:10]([OH:12])=[O:11])=[CH:5][CH:4]=1

Participants

5

Reactant 3

HCID 962WaterHCID 1118Sulfuric AcidHCID 59202209Ethyl 2-{4-[hydroxy(2-oxothiolan-3-yl)methyl]phenyl}propionate

Product 1

HCID 592021982-{4-[Hydroxy(2-oxothiolan-3-yl)methyl]phenyl}propionic acidYield 66.4%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

Ethyl 2-{4-[hydroxy(2-oxothiolan-3-yl)methyl]phenyl}propionate (106 mg) obtained in Example 32 was dissolved in 1,4-dioxane (2.0 ml), and to the solution was added 30% aqueous sulfuric acid (2.0 ml), and the solution was stirred overnight at room temperature. After completion of the reaction, to the reaction mixture was added water, and the mixture was extracted with ethyl acetate, and the organic layer was washed with water and saturated brine, and then dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure, and the residue was purified by silica gel column chromatography (chloroform/methanol=10/1) to give the title compound (64 mg, 66%).

Workup

  1. customAfter completion of the reaction
  2. extractionthe mixture was extracted with ethyl acetate
  3. washthe organic layer was washed with water and saturated brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customThe solvent was evaporated under reduced pressure
  6. customthe residue was purified by silica gel column chromatography (chloroform/methanol=10/1)

Sources & evidence

ORD record
ord-ca818b9643f9485fa74dc783da9a4343
Source dataset
uspto-grants-2012_04
Patent number
US08148421B2

Reaction notes

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