Potassium Carbonate → 2-(4-Methoxy-benzenesulfonyl)-2-methyl-3-[4-(2-piperidin-1-yl-ethoxy)-phenyl]propionic acid ethyl ester

HRID 1387697Notes

Reaction equation

HRID 1387697 reaction equation
[CH2:1]([O:3][C:4](=[O:18])[CH:5]([S:7]([C:10]1[CH:15]=[CH:14][C:13]([O:16][CH3:17])=[CH:12][CH:11]=1)(=[O:9])=[O:8])[CH3:6])[CH3:2].[N:19]1([CH2:25][CH2:26][O:27][C:28]2[CH:35]=[CH:34][C:31]([CH2:32]Cl)=[CH:30][CH:29]=2)[CH2:24][CH2:23][CH2:22][CH2:21][CH2:20]1.C([O-])([O-])=O.[K+].[K+].C1OCCOCCOCCOCCOCCOC1>CC(C)=O>[CH2:1]([O:3][C:4](=[O:18])[C:5]([S:7]([C:10]1[CH:11]=[CH:12][C:13]([O:16][CH3:17])=[CH:14][CH:15]=1)(=[O:8])=[O:9])([CH3:6])[CH2:32][C:31]1[CH:34]=[CH:35][C:28]([O:27][CH2:26][CH2:25][N:19]2[CH2:24][CH2:23][CH2:22][CH2:21][CH2:20]2)=[CH:29][CH:30]=1)[CH3:2]

Participants

6

Reactant 4

HCID 11430Potassium CarbonateHCID 2855718-Crown-6HCID 98607864-(2-Piperidin-1-yl-ethoxy)benzyl chlorideHCID 206605032-(4-Methoxy-benzenesulfonyl)propionic acid ethyl ester

Product 1

HCID 109619852-(4-Methoxy-benzenesulfonyl)-2-methyl-3-[4-(2-piperidin-1-yl-ethoxy)-phenyl]propionic acid ethyl esterYield 98%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

To a stirred mixture of 2.7 g (10 mmol) of 2-(4-methoxy-benzenesulfonyl)propionic acid ethyl ester, 3.03 gm (10 mmol) 4-(2-piperidin-1-yl-ethoxy)benzyl chloride, 10 gm of K2CO3 and 500 mg of 18-crown-6 in 250 ml of acetone was refluxed for 16 hours. At the end, the reaction mixture was filtered and the acetone layer was concentrated to a residue. The residue was extracted with chloroform, washed well with water, dried over anhydrous MgSO4, filtered and concentrated to a residue. The residue obtained was purified by silica-gel column chromatography by eluting with 50% ethyl acetate-hexanes to afford 4.8 gm (92%) of the desired product as an oil. MS: 490(M+H)+.

Workup

  1. temperaturewas refluxed for 16 hours
  2. filtrationAt the end, the reaction mixture was filtered
  3. concentrationthe acetone layer was concentrated to a residue
  4. extractionThe residue was extracted with chloroform
  5. washwashed well with water
  6. dry with materialdried over anhydrous MgSO4
  7. filtrationfiltered
  8. concentrationconcentrated to a residue
  9. customThe residue obtained
  10. customwas purified by silica-gel column chromatography
  11. washby eluting with 50% ethyl acetate-hexanes

Sources & evidence

ORD record
ord-b7de7d5f4f1b434c97e19cb4a9d1e81b
Source dataset
uspto-grants-2001_07
Patent number
US06268504B1

Reaction notes

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