Hydrochloric Acid → (2S)-2-Ethoxy-3-[4-(2-{ethyl[4-(trifluoromethoxy)benzyl]amino}-2-oxoethoxy)phenyl]propanoic Acid

HRID 1725221Notes

Reaction equation

HRID 1725221 reaction equation
[CH2:1]([O:3][C@@H:4]([CH2:10][C:11]1[CH:16]=[CH:15][C:14]([O:17][CH2:18][C:19]([N:21]([CH2:34][CH3:35])[CH2:22][C:23]2[CH:28]=[CH:27][C:26]([O:29][C:30]([F:33])([F:32])[F:31])=[CH:25][CH:24]=2)=[O:20])=[CH:13][CH:12]=1)[C:5]([O:7]CC)=[O:6])[CH3:2].[Li+].[OH-].Cl>C1COCC1>[CH2:1]([O:3][C@@H:4]([CH2:10][C:11]1[CH:16]=[CH:15][C:14]([O:17][CH2:18][C:19]([N:21]([CH2:34][CH3:35])[CH2:22][C:23]2[CH:28]=[CH:27][C:26]([O:29][C:30]([F:32])([F:33])[F:31])=[CH:25][CH:24]=2)=[O:20])=[CH:13][CH:12]=1)[C:5]([OH:7])=[O:6])[CH3:2]

Participants

5

Reactant 3

HCID 313Hydrochloric Acid2×HCID 3939Lithium HydroxideHCID 68855225HCID 68855225, compound

Product 1

HCID 68857797(2S)-2-Ethoxy-3-[4-(2-{ethyl[4-(trifluoromethoxy)benzyl]amino}-2-oxoethoxy)phenyl]propanoic AcidYield 87%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of ethyl(2S)-2-ethoxy-3-[4-(2-{ethyl[4-(trifluoromethoxy)benzyl]amino}-2-oxoethoxy)phenyl]propanoate (0.560 g, 1.13 mmol) in THF (50 mL) was added aqueous 0.10 M LiOH (25 mL) and the solution 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 (2×50 mL). The combined organic phase was washed with brine (50 mL), dried over Na2SO4, and concentrated in vacuo. Purification on a prepacked column of silica gel (Isolute® SPE Column, 10 g/70 mL) with ethyl acetate as the eluent afforded 0.457 g (87%) of a colourless oil.

Workup

  1. extractionextracted with ethyl acetate (2×50 mL)
  2. washThe combined organic phase was washed with brine (50 mL)
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated in vacuo
  5. customPurification on a prepacked column of silica gel (Isolute® SPE Column, 10 g/70 mL) with ethyl acetate as the eluent

Sources & evidence

ORD record
ord-56d9d0d7831b42129df992a45843e2bc
Source dataset
uspto-grants-2009_02
Patent number
US07488844B2

Reaction notes

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