Hydrochloric Acid → (2S)-3-(4-{2-[Butyl(2,3-dimethoxybenzyl)amino]-2-oxoethoxy}phenyl)-2-ethoxypropanoic acid

HRID 1725243Notes

Reaction equation

HRID 1725243 reaction equation
[CH3:1][O:2][C:3]1[C:34]([O:35][CH3:36])=[CH:33][CH:32]=[CH:31][C:4]=1[CH2:5][N:6]([CH2:27][CH2:28][CH2:29][CH3:30])[C:7](=[O:26])[CH2:8][O:9][C:10]1[CH:15]=[CH:14][C:13]([CH2:16][C@H:17]([O:23][CH2:24][CH3:25])[C:18]([O:20]CC)=[O:19])=[CH:12][CH:11]=1.[Li+].[OH-].Cl>C(#N)C>[CH2:27]([N:6]([CH2:5][C:4]1[CH:31]=[CH:32][CH:33]=[C:34]([O:35][CH3:36])[C:3]=1[O:2][CH3:1])[C:7](=[O:26])[CH2:8][O:9][C:10]1[CH:11]=[CH:12][C:13]([CH2:16][C@H:17]([O:23][CH2:24][CH3:25])[C:18]([OH:20])=[O:19])=[CH:14][CH:15]=1)[CH2:28][CH2:29][CH3:30]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 68858245Ethyl (2S)-3-(4-{2-[butyl(2,3-dimethoxybenzyl)amino]-2-oxoethoxy}phenyl)-2-ethoxypropanoate

Product 1

HCID 11294425(2S)-3-(4-{2-[Butyl(2,3-dimethoxybenzyl)amino]-2-oxoethoxy}phenyl)-2-ethoxypropanoic acidYield 101.4%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a solution of ethyl(2S)-3-(4-{2-[(2,3-dimethoxybenzyl)(butyl)amino]-2-oxoethoxy}phenyl)-2-ethoxypropanoate (1.02 g, 2.0 mmol) in acetonitrile (80 mL) was added aqueous 0.10 M LiOH (40 mL) and the reaction mixture was stirred at room temperature overnight. 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 (75 mL), dried over Na2SO4, and concentrated in vacuo to afford 0.96 g (98%) of a light yellow oil.

Workup

  1. extractionextracted with ethyl acetate (3×100 mL)
  2. washThe combined organic phase was washed with brine (75 mL)
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-1f52d40e3fc04bb9af46c50bcca7df95
Source dataset
uspto-grants-2009_02
Patent number
US07488844B2

Reaction notes

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