Dichloromethane → 2-Acetoxy-4-((1-(methylsulfonyl)piperidin-4-yl)oxy)benzoic acid

HRID 454488Notes

Reaction equation

HRID 454488 reaction equation
[C:1](OC(=O)C)(=[O:3])[CH3:2].C(Cl)Cl.[OH:11][C:12]1[CH:20]=[C:19]([O:21][CH:22]2[CH2:27][CH2:26][N:25]([S:28]([CH3:31])(=[O:30])=[O:29])[CH2:24][CH2:23]2)[CH:18]=[CH:17][C:13]=1[C:14]([OH:16])=[O:15]>N1C=CC=CC=1>[C:1]([O:11][C:12]1[CH:20]=[C:19]([O:21][CH:22]2[CH2:23][CH2:24][N:25]([S:28]([CH3:31])(=[O:30])=[O:29])[CH2:26][CH2:27]2)[CH:18]=[CH:17][C:13]=1[C:14]([OH:16])=[O:15])(=[O:3])[CH3:2]

Participants

5

Reactant 3

HCID 6344DichloromethaneHCID 7918Acetic Anhydride2×HCID 669904182-Hydroxy-4-((1-(methylsulfonyl)piperidin-4-yl)oxy)benzoic acid

Product 1

HCID 669903912-Acetoxy-4-((1-(methylsulfonyl)piperidin-4-yl)oxy)benzoic acid

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent2×

Procedure

Under ice-cooling, pyridine (0.12 mL) and acetic anhydride (0.065 mL) were sequentially added to a methylene chloride (1.8 mL) suspension of the obtained 2-hydroxy-4-((1-(methylsulfonyl)piperidin-4-yl)oxy)benzoic acid (0.18 g), followed by stirring at room temperature for 1 hour. Under ice-cooling, pyridine (0.023 mL) and acetic anhydride (0.016 mL) were sequentially added to the reaction mixture, followed by stirring at room temperature for 2 hours. The solvent was evaporated under reduced pressure, and 1 mol/L hydrochloric acid and ethyl acetate were added to the residue. The organic layer was separated, washed with 1 mol/L hydrochloric acid, water, and a saturated aqueous solution of sodium chloride sequentially, and dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure. Diisopropyl ether was added to the obtained residue, and the solid substance was collected by filtration to obtain 0.18 g of 2-acetoxy-4-((1-(methylsulfonyl)piperidin-4-yl)oxy)benzoic acid as a white solid.

Workup

  1. temperatureUnder ice-cooling
  2. temperatureUnder ice-cooling
  3. stirringby stirring at room temperature for 2 hours
  4. customThe solvent was evaporated under reduced pressure, and 1 mol/L hydrochloric acid and ethyl acetate
  5. additionwere added to the residue
  6. customThe organic layer was separated
  7. washwashed with 1 mol/L hydrochloric acid, water
  8. dry with materiala saturated aqueous solution of sodium chloride sequentially, and dried over anhydrous magnesium sulfate
  9. customthe solvent was evaporated under reduced pressure
  10. additionDiisopropyl ether was added to the obtained residue
  11. filtrationthe solid substance was collected by filtration

Sources & evidence

ORD record
ord-f3f7457551784b73824bf9ef2d14a0dd
Source dataset
uspto-grants-2013_07
Patent number
US08492582B2

Reaction notes

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