Lithium Hydroxide → HCID 22988677, compound

HRID 987338Notes

Reaction equation

HRID 987338 reaction equation
C([O:3][C:4](=[O:31])[CH:5]([O:28][CH2:29][CH3:30])[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]([C:22]([NH:24][CH:25]([CH3:27])[CH3:26])=[O:23])=[CH:18][CH:17]=2)=[CH:9][CH:8]=1)C.[OH-].[Li+].[OH-].[Na+]>O1CCCC1.O>[CH2:29]([O:28][CH:5]([CH2:6][C:7]1[CH:12]=[CH:11][C:10]([O:13][CH2:14][CH2:15][C:16]2[CH:17]=[CH:18][C:19]([C:22]([NH:24][CH:25]([CH3:26])[CH3:27])=[O:23])=[CH:20][CH:21]=2)=[CH:9][CH:8]=1)[C:4]([OH:31])=[O:3])[CH3:30]

Participants

6

Reactant 3

HCID 3939Lithium HydroxideHCID 14798Sodium HydroxideHCID 57131206HCID 57131206, compound

Product 1

HCID 22988677HCID 22988677, compoundYield 68.8%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent3×HCID 8028TetrahydrofuranSolvent

Procedure

2-Ethoxy-3-[4-(2-{4-(isopropylaminocarbonyl)phenyl}ethoxy)phenyl]propanoic acid ethyl ester (described in Example 106) (1 g; 2.34 mmole) was dissolved in tetrahydrofuran (10 ml). Lithium hydroxide (0.056 g; 2.34 mmole) dissolved in water (6 ml) was added slowly in portions during 20 minutes. The reaction mixture was stirred at room temperature for 3 hours and then diluted with water followed by careful evaporation of tetrahydrofuran. The residual water phase was extracted once with diethyl ether, then acidified and extracted with ethyl acetate. The ethyl acetate phase was washed with brine, dried with sodium sulfate and evaporated. The residue was dissolved in methanol (10 ml) and sodium hydroxide (0.109 g; 1.73 mmole) in water (3.5 ml) was added. The solution was evaporated and the residue redissolved in water. Freeze drying gave 0.643 g (65.2% yield) of 2-ethoxy-3-[4-(2-{4-(isopropylaminocarbonyl)phenyl}ethoxy)phenyl]propanoic acid.

Workup

  1. additionwas added slowly in portions during 20 minutes
  2. customfollowed by careful evaporation of tetrahydrofuran
  3. extractionThe residual water phase was extracted once with diethyl ether
  4. extractionextracted with ethyl acetate
  5. washThe ethyl acetate phase was washed with brine
  6. dry with materialdried with sodium sulfate
  7. customevaporated
  8. dissolutionThe residue was dissolved in methanol (10 ml)
  9. customThe solution was evaporated
  10. dissolutionthe residue redissolved in water
  11. customFreeze drying

Sources & evidence

ORD record
ord-d2e84f5cbaf14e8d8b9426d203e434b1
Source dataset
uspto-grants-2003_10
Patent number
US06630600B1

Reaction notes

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