Lithium Hydroxide → (2S)-3-[4-(2-{Butyl[4-(trifluoromethyl)benzyl]amino}-2-oxoethoxy)phenyl]-2-ethoxy Propanoic Acid

HRID 1725225Notes

Reaction equation

HRID 1725225 reaction equation
[CH2:1]([N:5]([CH2:26][C:27]1[CH:32]=[CH:31][C:30]([C:33]([F:36])([F:35])[F:34])=[CH:29][CH:28]=1)[C:6](=[O:25])[CH2:7][O:8][C:9]1[CH:14]=[CH:13][C:12]([CH2:15][C@H:16]([O:22][CH2:23][CH3:24])[C:17]([O:19]CC)=[O:18])=[CH:11][CH:10]=1)[CH2:2][CH2:3][CH3:4].[Li+].[OH-]>C(#N)C>[CH2:1]([N:5]([CH2:26][C:27]1[CH:32]=[CH:31][C:30]([C:33]([F:34])([F:35])[F:36])=[CH:29][CH:28]=1)[C:6](=[O:25])[CH2:7][O:8][C:9]1[CH:10]=[CH:11][C:12]([CH2:15][C@H:16]([O:22][CH2:23][CH3:24])[C:17]([OH:19])=[O:18])=[CH:13][CH:14]=1)[CH2:2][CH2:3][CH3:4]

Participants

4

Reactant 2

HCID 3939Lithium HydroxideHCID 68856874Ethyl(2S)-3-[4-(2-{butyl[4-(trifluoromethyl)benzyl]amino}-2-oxoethoxy)phenyl]-2-ethoxypropanoate

Product 1

HCID 68855342(2S)-3-[4-(2-{Butyl[4-(trifluoromethyl)benzyl]amino}-2-oxoethoxy)phenyl]-2-ethoxy Propanoic AcidYield 79%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a solution of ethyl(2S)-3-[4-(2-{butyl[4-(trifluoromethyl)benzyl]amino}-2-oxoethoxy)phenyl]-2-ethoxypropanoate (0.311 g, 0.61 mmol) in acetonitrile (30 mL) was added aqueous 0.10 M LiOH (15 mL) and the solution was stirred at room temperature overnight. After acidification with 5% HCl, the mixture was extracted with ethyl acetate (3×100 mL) and the combined organic phase was washed with 5% HCl (100 mL) and brine (100 mL), dried over Na2SO4, and concentrated in vacuo to afford 0.232 g (79%) of a colourless oil.

Workup

  1. extractionAfter acidification with 5% HCl, the mixture was extracted with ethyl acetate (3×100 mL)
  2. washthe combined organic phase was washed with 5% HCl (100 mL) and brine (100 mL)
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-39f420d17a304c24a172b170f5486ec9
Source dataset
uspto-grants-2009_02
Patent number
US07488844B2

Reaction notes

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