Hydrochloric Acid → HCID 66751355, compound

HRID 534930Notes

Reaction equation

HRID 534930 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[CH2:13][CH2:12][N:11]([C:14](=[O:21])[CH2:15][C:16]([O:18]CC)=[O:17])[CH2:10][CH2:9]2)=[C:4]([C:22]([CH3:25])([CH3:24])[CH3:23])[CH:3]=1.[OH-].[Li+].Cl>C1COCC1>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[CH2:13][CH2:12][N:11]([C:14](=[O:21])[CH2:15][C:16]([OH:18])=[O:17])[CH2:10][CH2:9]2)=[C:4]([C:22]([CH3:25])([CH3:24])[CH3:23])[CH:3]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 66750881HCID 66750881, compound

Product 1

HCID 66751355HCID 66751355, compoundYield 102.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of ethyl 3-[4-(4-bromo-2-tert-butylphenyl)piperazin-1-yl]-3-oxopropanoate (Example 68, 0.280 g, 0.681 mmol) in THF (5 mL) stirring at 0° C. was added 1 M lithium hydroxide solution (5 mL, 5 mmol). After 2 h the reaction mixture was acidified with 1 M hydrochloric acid solution and extracted with ethyl acetate. The organic layer was washed with brine, dried over MgSO4, and the solvent was evaporated under reduced pressure to provide 3-[4-(4-bromo-2-tert-butylphenyl)piperazin-1-yl]-3-oxopropanoic acid (0.267 g, quant) as a white powder.

Workup

  1. extractionextracted with ethyl acetate
  2. washThe organic layer was washed with brine
  3. dry with materialdried over MgSO4
  4. customthe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-46dc23b621644e8bb6a58592f9b74df6
Source dataset
uspto-grants-2014_10
Patent number
US08853215B2

Reaction notes

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