Sulfuric Acid → HCID 24782883, compound

HRID 1685805Notes

Reaction equation

HRID 1685805 reaction equation
C([C:3]1([CH2:9][C:10]2[CH:15]=[CH:14][C:13]([CH:16]([CH3:20])[C:17]([OH:19])=[O:18])=[CH:12][CH:11]=2)[C:7](=[O:8])[CH2:6][S:5][CH2:4]1)#N.S(=O)(=O)(O)O>O1CCOCC1>[O:8]=[C:7]1[CH2:6][S:5][CH2:4][CH:3]1[CH2:9][C:10]1[CH:15]=[CH:14][C:13]([CH:16]([CH3:20])[C:17]([OH:19])=[O:18])=[CH:12][CH:11]=1

Participants

4

Reactant 2

HCID 1118Sulfuric AcidHCID 24782635HCID 24782635, compound

Product 1

HCID 24782883HCID 24782883, compoundYield 50%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
110 °C

Procedure

2-[4-(3-Cyano-4-oxothiolan-3-ylmethyl)phenyl]propionic acid (1.27 g) obtained in Example 7 was dissolved in 1,4-dioxane (10.0 ml), 30% aqueous sulfuric acid (10.0 ml) was added to the solution and stirred overnight at 110° C. The reaction mixture was quenched with water, and extracted with ethyl acetate. The organic layer was washed with water and saturated brine, and then dried over sodium sulfate. The solvent was evaporated under reduced pressure, and then the residue was purified by silica gel column chromatography (hexane/ethyl acetate=1/1) to give the title compound (550 mg, 50%).

Workup

  1. customThe reaction mixture was quenched with water
  2. extractionextracted with ethyl acetate
  3. washThe organic layer was washed with water and saturated brine
  4. dry with materialdried over sodium sulfate
  5. customThe solvent was evaporated under reduced pressure
  6. customthe residue was purified by silica gel column chromatography (hexane/ethyl acetate=1/1)

Sources & evidence

ORD record
ord-bc9beeb42fbd47b7b9ac90f22425b9ae
Source dataset
uspto-grants-2012_04
Patent number
US08148421B2

Reaction notes

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