Lithium hydroxide, monohydrate → 2-Ethoxy-3-{4-[2-(4-methanesulfonylaminophenyl)ethoxy]phenyl}propanoic acid

HRID 987307Notes

Reaction equation

HRID 987307 reaction equation
C([O:3][C:4](=[O:30])[CH:5]([O:27][CH2:28][CH3:29])[CH2:6][C:7]1[CH:12]=[CH:11][C:10]([O:13][CH2:14][CH2:15][C:16]2[CH:21]=[CH:20][C:19]([NH:22][S:23]([CH3:26])(=[O:25])=[O:24])=[CH:18][CH:17]=2)=[CH:9][CH:8]=1)C.O.[OH-].[Li+]>O1CCCC1.O>[CH2:28]([O:27][CH:5]([CH2:6][C:7]1[CH:8]=[CH:9][C:10]([O:13][CH2:14][CH2:15][C:16]2[CH:17]=[CH:18][C:19]([NH:22][S:23]([CH3:26])(=[O:24])=[O:25])=[CH:20][CH:21]=2)=[CH:11][CH:12]=1)[C:4]([OH:30])=[O:3])[CH3:29]

Participants

5

Reactant 2

HCID 168937Lithium hydroxide, monohydrateHCID 54054669HCID 54054669, compound

Product 1

HCID 99093362-Ethoxy-3-{4-[2-(4-methanesulfonylaminophenyl)ethoxy]phenyl}propanoic acidYield 104.3%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

2-Ethoxy-3-{4-[2-(4-methanesulfonylaminophenyl)ethoxy]phenyl}propanoic acid ethyl ester (described in Example 62) (0.554 g; 1.27 mmole) was dissolved in tetrahydrofuran (5.7 ml). Lithium hydroxide hydrate (0.137 g; 3,26 mmole) was dissolved in water and added in portions during 30 minutes at room temperature. The reaction mixture was kept in the refrigerator over night. Tetrahydrofuran was evaporated in vacuo. The water residue was washed with ethyl acetate, acidified with hydrochloric acid (1M) to pH 1-2 and the mixture was extracted with ethyl acetate. The organic phase was washed with brine, dried (sodium sulfate), filtered and the solvent was evaporated in vacuo to give 0.54 g (yield 100%) of 2-ethoxy-3-{4-[2-(4-methanesulfonylaminophenyl)ethoxy]phenyl}propanoic acid.

Workup

  1. additionadded in portions during 30 minutes at room temperature
  2. waitThe reaction mixture was kept in the refrigerator over night
  3. customTetrahydrofuran was evaporated in vacuo
  4. washThe water residue was washed with ethyl acetate
  5. extractionthe mixture was extracted with ethyl acetate
  6. washThe organic phase was washed with brine
  7. dry with materialdried (sodium sulfate)
  8. filtrationfiltered
  9. customthe solvent was evaporated in vacuo

Sources & evidence

ORD record
ord-ab31c29587194e13942254b04e423e96
Source dataset
uspto-grants-2003_10
Patent number
US06630600B1

Reaction notes

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