Hydrochloric Acid → (2S)-3-[4-(2-{Butyl[2-fluoro-4-(trifluoromethyl)benzyl]amino}-2-oxoethoxy)phenyl]-2-ethoxypropanoic Acid

HRID 1725215Notes

Reaction equation

HRID 1725215 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][C:28]=1[F:37])[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-].Cl>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][C:28]=1[F:37])[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]([OH:19])=[O:18])=[CH:11][CH:10]=1)[CH2:2][CH2:3][CH3:4]

Participants

5

Reactant 3

HCID 313Hydrochloric Acid2×HCID 3939Lithium HydroxideHCID 68855512Ethyl(2S)-3-[4-(2-{butyl[2-fluoro-4-(trifluoromethyl)benzyl]amino}-2-oxoethoxy)phenyl]-2-ethoxypropanoate

Product 1

HCID 9957584(2S)-3-[4-(2-{Butyl[2-fluoro-4-(trifluoromethyl)benzyl]amino}-2-oxoethoxy)phenyl]-2-ethoxypropanoic AcidYield 97%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a solution of ethyl(2S)-3-[4-(2-{butyl[2-fluoro-4-(trifluoromethyl)benzyl]amino}-2-oxoethoxy)phenyl]-2-ethoxypropanoate (0.748 g, 1.42 mmol) in acetonitrile (70 mL) was added aqueous 0.10 M LiOH (35 mL) and the reaction mixture was stirred at room temperature overnight. After neutralisation with 5% HCl, the solvent volume was reduced in vacuo and the remaining aqueous phase was acidified with 5% HCl and extracted with ethyl acetate (3×100 mL). The combined organic phase was washed with brine (100 mL), dried over Na2SO4, and concentrated in vacuo to afford 0.688 g (97%) of a pale yellow oil.

Workup

  1. extractionextracted with ethyl acetate (3×100 mL)
  2. washThe combined organic phase was washed with brine (100 mL)
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-3559b8194ce345c8843629efe4459f87
Source dataset
uspto-grants-2009_02
Patent number
US07488844B2

Reaction notes

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