Hydrochloric Acid → HCID 66792804, compound

HRID 534961Notes

Reaction equation

HRID 534961 reaction equation
[C:1]([C:5]1[CH:10]=[C:9]([C:11]([OH:14])([CH3:13])[CH3:12])[CH:8]=[CH:7][C:6]=1[N:15]1[CH2:20][CH2:19][N:18]([C:21](=[O:27])[C:22]([O:24]CC)=[O:23])[CH2:17][CH2:16]1)([CH3:4])([CH3:3])[CH3:2].[OH-].[Li+].Cl>C1COCC1>[C:1]([C:5]1[CH:10]=[C:9]([C:11]([OH:14])([CH3:13])[CH3:12])[CH:8]=[CH:7][C:6]=1[N:15]1[CH2:16][CH2:17][N:18]([C:21](=[O:27])[C:22]([OH:24])=[O:23])[CH2:19][CH2:20]1)([CH3:2])([CH3:3])[CH3:4]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 66751254HCID 66751254, compound

Product 1

HCID 66792804HCID 66792804, compoundYield 95%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of ethyl {4-[2-tert-butyl-4-(1-hydroxy-1-methylethyl)phenyl]piperazin-1-yl}(oxo)acetate (Example 167, 0.38 g, 1.01 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 {4-[2-tert-butyl-4-(1-hydroxy-1-methylethyl)phenyl]piperazin-1-yl}(oxo)acetic acid (0.333 g, 95%) as a pale yellow 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-4d75be46471245bdacb18f065b862ec2
Source dataset
uspto-grants-2014_10
Patent number
US08853215B2

Reaction notes

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