Hydrochloric Acid → [4-({[4-(2-Tert-butylphenyl)piperazin-1-yl]carbonyl}amino)phenoxy]acetic acid

HRID 534968Notes

Reaction equation

HRID 534968 reaction equation
[C:1]([C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[N:11]1[CH2:16][CH2:15][N:14]([C:17]([NH:19][C:20]2[CH:31]=[CH:30][C:23]([O:24][CH2:25][C:26]([O:28]C)=[O:27])=[CH:22][CH:21]=2)=[O:18])[CH2:13][CH2:12]1)([CH3:4])([CH3:3])[CH3:2].[OH-].[Li+].Cl>C1COCC1>[C:1]([C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[N:11]1[CH2:12][CH2:13][N:14]([C:17]([NH:19][C:20]2[CH:21]=[CH:22][C:23]([O:24][CH2:25][C:26]([OH:28])=[O:27])=[CH:30][CH:31]=2)=[O:18])[CH2:15][CH2:16]1)([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 66751108Methyl [4-({[4-(2-tert-butylphenyl)piperazin-1-yl]carbonyl}amino)phenoxy]acetate

Product 1

HCID 66792782[4-({[4-(2-Tert-butylphenyl)piperazin-1-yl]carbonyl}amino)phenoxy]acetic acidYield 98.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To an ice-cold stirred solution of methyl [4-({[4-(2-tert-butylphenyl)piperazin-1-yl]carbonyl}amino)phenoxy]acetate (Example 175, 0.240 g, 0.564 mmol) in THF (5 mL) was added 1 M lithium hydroxide solution (5 mL, 5 mmol). After 1 h the reaction mixture was acidified with 1 M HCl solution and extracted with ethyl acetate. The organic layer was washed with brine, dried over MgSO4, filtered and concentrated under reduced pressure to provide [4-({[4-(2-tert-butylphenyl)piperazin-1-yl]carbonyl}amino)phenoxy]acetic acid (0.228 g, 98%) 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. filtrationfiltered
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-f50883a9dc9b44299a341cf632262d48
Source dataset
uspto-grants-2014_10
Patent number
US08853215B2

Reaction notes

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