Hydrochloric Acid → 2-Ethoxy-3-{4-[2-(4-phenylmethanesulfonyloxy-phenyl)ethoxy]phenyl}propanoic acid

HRID 987256Notes

Reaction equation

HRID 987256 reaction equation
C([O:3][C:4](=[O:36])[CH:5]([O:33][CH2:34][CH3:35])[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]([O:22][S:23]([CH2:26][C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=3)(=[O:25])=[O:24])=[CH:18][CH:17]=2)=[CH:9][CH:8]=1)C.[OH-].[Li+].Cl>O1CCCC1.O>[CH2:34]([O:33][CH:5]([CH2:6][C:7]1[CH:8]=[CH:9][C:10]([O:13][CH2:14][CH2:15][C:16]2[CH:21]=[CH:20][C:19]([O:22][S:23]([CH2:26][C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=3)(=[O:24])=[O:25])=[CH:18][CH:17]=2)=[CH:11][CH:12]=1)[C:4]([OH:36])=[O:3])[CH3:35]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 865950622-Ethoxy-3-{4-[2-(4-phenylmethanesulfonyloxyphenyl)ethoxy]phenyl}propanoic acid ethyl ester

Product 1

HCID 865950632-Ethoxy-3-{4-[2-(4-phenylmethanesulfonyloxy-phenyl)ethoxy]phenyl}propanoic acidYield 92.6%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

2-Ethoxy-3-{4-[2-(4-phenylmethanesulfonyloxyphenyl)ethoxy]phenyl}propanoic acid ethyl ester (described in Example 30) (0.21 g; 0.41 mmol) was dissolved in tetrahydrofuran (4 ml) and lithium hydroxide (0.021 g; 0.48 mmol) dissolved in water (1 ml) was added dropwise. The resulting solution was stirred at room temperature over night and then acidified with hydrochloric acid (2M). Extraction with ethyl acetate, drying with magnesium sulfate and evaporation gave 0.184 g (92%) of 2-ethoxy-3-{4-[2-(4-phenylmethanesulfonyloxy-phenyl)ethoxy]phenyl}propanoic acid as an oil.

Workup

  1. additionwas added dropwise
  2. extractionExtraction with ethyl acetate
  3. dry with materialdrying with magnesium sulfate and evaporation

Sources & evidence

ORD record
ord-55b8707d1649400b9a56aaca697ec0c5
Source dataset
uspto-grants-2003_10
Patent number
US06630600B1

Reaction notes

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