Hydrochloric Acid → HCID 11398134, compound

HRID 1725234Notes

Reaction equation

HRID 1725234 reaction equation
[F:1][C:2]1[CH:38]=[C:37]([F:39])[CH:36]=[CH:35][C:3]=1[CH2:4][N:5]([CH2:26][C:27]1[CH:32]=[CH:31][C:30]([CH2:33][CH3:34])=[CH:29][CH:28]=1)[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.[Li+].[OH-].Cl>C(#N)C>[F:1][C:2]1[CH:38]=[C:37]([F:39])[CH:36]=[CH:35][C:3]=1[CH2:4][N:5]([CH2:26][C:27]1[CH:28]=[CH:29][C:30]([CH2:33][CH3:34])=[CH:31][CH:32]=1)[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

Participants

5

Reactant 3

HCID 313Hydrochloric Acid2×HCID 3939Lithium HydroxideHCID 68854106HCID 68854106, compound

Product 1

HCID 11398134HCID 11398134, compoundYield 94%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a solution of ethyl(2S)-3-(4-{2-[(2,4-difluorobenzyl)(4-ethylbenzyl)amino]-2-oxoethoxy}phenyl)-2-ethoxypropanoate (1.13 g, 2.1 mmol) in acetonitrile (100 mL) was added aqueous 0.10 M LiOH (52 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 (3×100 mL). The combined organic phase was washed with brine (100 mL), dried over Na2SO4, and concentrated in vacuo to afford 1.01 g (94%) of a colourless 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-9f08f56cf048497dac791ef68e88c87f
Source dataset
uspto-grants-2009_02
Patent number
US07488844B2

Reaction notes

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