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

HRID 987268Notes

Reaction equation

HRID 987268 reaction equation
C[O:2][C:3](=[O:32])[CH:4]([O:29][CH2:30][CH3:31])[CH2:5][C:6]1[CH:11]=[CH:10][C:9]([O:12][CH2:13][CH2:14][C:15]2[CH:20]=[CH:19][C:18]([O:21][S:22]([CH3:25])(=[O:24])=[O:23])=[CH:17][CH:16]=2)=[CH:8][C:7]=1[N+:26]([O-:28])=[O:27].O.[OH-].[Li+]>O1CCCC1.O>[CH2:30]([O:29][CH:4]([CH2:5][C:6]1[CH:11]=[CH:10][C:9]([O:12][CH2:13][CH2:14][C:15]2[CH:20]=[CH:19][C:18]([O:21][S:22]([CH3:25])(=[O:24])=[O:23])=[CH:17][CH:16]=2)=[CH:8][C:7]=1[N+:26]([O-:28])=[O:27])[C:3]([OH:32])=[O:2])[CH3:31]

Participants

5

Reactant 2

HCID 168937Lithium hydroxide, monohydrateHCID 571861342-Ethoxy-3-[4-(2-{4-methylsulfonyloxyphenyl}ethoxy)-2-nitrophenyl]propanoic acid methyl ester

Product 1

HCID 229886802-Ethoxy-3-[4-(2-{4-methylsulfonyloxyphenyl}ethoxy)-2-nitropheny]propanoic acidYield 93%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

2-Ethoxy-3-[4-(2-{4-methylsulfonyloxyphenyl}ethoxy)-2-nitrophenyl]propanoic acid methyl ester (described in Example 35) (0.8 g; 1.71 mmole) was dissolved in tetrahydrofuran (8 ml). A solution of lithium hydroxide monohydrate (0.086 g; 2.05 mmole) in water (8 ml) was added under stirring. The reaction mixture was stirred at room temperature for 5 hours and then evaporated to remove tetrahydrofuran. The residue was extracted with diethyl ether, acidified to pH˜3 with hydrochloric acid (10%) and extracted with ethyl acetate. The organic phase was washed with water and brine, dried with magnesium sulfate. The solvent was removed and 0.72 g (93% yield) of 2-ethoxy-3-[4-(2-{4-methylsulfonyloxyphenyl}ethoxy)-2-nitropheny]propanoic acid was obtained.

Workup

  1. stirringThe reaction mixture was stirred at room temperature for 5 hours
  2. customevaporated
  3. customto remove tetrahydrofuran
  4. extractionThe residue was extracted with diethyl ether
  5. extractionextracted with ethyl acetate
  6. washThe organic phase was washed with water and brine
  7. dry with materialdried with magnesium sulfate
  8. customThe solvent was removed

Sources & evidence

ORD record
ord-294ea424d0564700b3db5de53f1bf708
Source dataset
uspto-grants-2003_10
Patent number
US06630600B1

Reaction notes

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