Hydrochloric Acid → HCID 11384129, compound

HRID 1725247Notes

Reaction equation

HRID 1725247 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]([CH2:30][CH3:31])[CH2:22][C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=2[F:29])=[O:20])=[CH:13][CH:12]=1)[C:5]([O:7]CC)=[O:6])[CH3:2].[Li+].[OH-].Cl>C(#N)C>[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]([CH2:30][CH3:31])[CH2:22][C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=2[F:29])=[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 68856104HCID 68856104, compound

Product 1

HCID 11384129HCID 11384129, compoundYield 95%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a solution of ethyl(2S)-2-ethoxy-3-(4-{2-[ethyl(2-fluorobenzyl)amino]-2-oxoethoxy}phenyl)propanoate (0.980 g, 2.27 mmol) in acetonitrile (120 mL) was added aqueous 0.10 M LiOH (57 mL) and the reaction mixture 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 brine (100 mL), dried over Na2SO4, and concentrated in vacuo to afford 0.868 g (95%) of a pale yellow oil.

Workup

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

Sources & evidence

ORD record
ord-dba35533205f4efeaf28812511472e16
Source dataset
uspto-grants-2009_02
Patent number
US07488844B2

Reaction notes

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