Hydrochloric Acid → (2S)-3-(4-{2-[1Benzyl(hexyl)amino]-2-oxoethoxy}phenyl)-2-ethoxypropanoic Acid

HRID 2109009Notes

Reaction equation

HRID 2109009 reaction equation
C([N:8]([CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH3:34])[C:9](=[O:28])[CH2:10][O:11][C:12]1[CH:17]=[CH:16][C:15]([CH2:18][C@H:19]([O:25][CH2:26][CH3:27])[C:20]([O:22]CC)=[O:21])=[CH:14][CH:13]=1)C1C=CC=CC=1.[Li+].[OH-].Cl>C1COCC1>[CH2:18]([CH:29]([NH:8][C:9](=[O:28])[CH2:10][O:11][C:12]1[CH:17]=[CH:16][C:15]([CH2:18][C@H:19]([O:25][CH2:26][CH3:27])[C:20]([OH:22])=[O:21])=[CH:14][CH:13]=1)[CH2:30][CH2:31][CH2:32][CH2:33][CH3:34])[C:15]1[CH:16]=[CH:17][CH:12]=[CH:13][CH:14]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 11248399Ethyl(2S)-3-(4-{2-[benzyl(hexyl)amino]-2-oxoethoxy}phenyl)-2-ethoxypropanoate

Product 1

HCID 68902695(2S)-3-(4-{2-[1Benzyl(hexyl)amino]-2-oxoethoxy}phenyl)-2-ethoxypropanoic AcidYield 181.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of ethyl(2S)-3-(4-{2-[benzyl(hexyl)amino]-2-oxoethoxy}phenyl)-2-ethoxypropanoate (0.080 g, 0.17 mmol) in THF (8.6 mL) was added 4.3 mL of a 0.10 M LiOH solution and the reaction mixture was stirred at room temperature overnight. The reaction mixture was acidified with 2M HCl and extracted with ethyl acetate (3×25mL). The combined organic phase was washed with brine (25 μL), dried over Na2SO4, and concentrated in vacuo to afford 0.068 g (90%) of a colourless oil.

Workup

  1. extractionextracted with ethyl acetate (3×25mL)
  2. washThe combined organic phase was washed with brine (25 μL)
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-5e11cb6aa85a461da9d8cd1e82b39d64
Source dataset
uspto-grants-2009_04
Patent number
US07514471B2

Reaction notes

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