Hydrochloric Acid → (2S)-3-(4-{2-[(4-Chlorobenzyl)(ethyl)amino]-2-oxoethoxy}phenyl)-2-ethoxypropanoic Acid

HRID 1725217Notes

Reaction equation

HRID 1725217 reaction equation
[Cl:1][C:2]1[CH:31]=[CH:30][C:5]([CH2:6][N:7]([CH2:28][CH3:29])[C:8](=[O:27])[CH2:9][O:10][C:11]2[CH:16]=[CH:15][C:14]([CH2:17][C@H:18]([O:24][CH2:25][CH3:26])[C:19]([O:21]CC)=[O:20])=[CH:13][CH:12]=2)=[CH:4][CH:3]=1.[Li+].[OH-].Cl>C1COCC1>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:6][N:7]([CH2:28][CH3:29])[C:8](=[O:27])[CH2:9][O:10][C:11]2[CH:16]=[CH:15][C:14]([CH2:17][C@H:18]([O:24][CH2:25][CH3:26])[C:19]([OH:21])=[O:20])=[CH:13][CH:12]=2)=[CH:30][CH:31]=1

Participants

5

Reactant 3

HCID 313Hydrochloric Acid2×HCID 3939Lithium HydroxideHCID 68856731Ethyl(2S)-3-(4-{2-[(4-chlorobenzyl)(ethyl)amino]-2-oxoethoxy}phenyl)-2-ethoxypropanoate

Product 1

HCID 68856723(2S)-3-(4-{2-[(4-Chlorobenzyl)(ethyl)amino]-2-oxoethoxy}phenyl)-2-ethoxypropanoic AcidYield 61%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of ethyl(2S)-3-(4-{2-[(4-chlorobenzyl)(ethyl)amino]-2-oxoethoxy}phenyl)-2-ethoxypropanoate (0.240 g, 0.54 mmol) in THF (30 mL) was added aqueous 0.10 M LiOH (15 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 methylene chloride (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, 2 g/15 mL) with ethyl acetate as the eluent afforded 0.138 g (61%) of a pale yellow oil.

Workup

  1. extractionextracted with methylene chloride (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, 2 g/15 mL) with ethyl acetate as the eluent

Sources & evidence

ORD record
ord-f857f7770d09479795b841b470cd350d
Source dataset
uspto-grants-2009_02
Patent number
US07488844B2

Reaction notes

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