Tert-butyl 4-(4-(4-(1,1-dimethylethoxycarbonyl)piperazin-1-yl)phenylaminocarbonyl)phenoxyacetate → 4-(4-(Piperazin-1-yl)phenylaminocarbonyl)phenoxyacetic acid

HRID 1459425Notes

Reaction equation

HRID 1459425 reaction equation
CC(C)(OC([N:7]1[CH2:12][CH2:11][N:10]([C:13]2[CH:18]=[CH:17][C:16]([NH:19][C:20]([C:22]3[CH:36]=[CH:35][C:25]([O:26][CH2:27][C:28]([O:30]C(C)(C)C)=[O:29])=[CH:24][CH:23]=3)=[O:21])=[CH:15][CH:14]=2)[CH2:9][CH2:8]1)=O)C>CCOC(C)=O>[N:10]1([C:13]2[CH:18]=[CH:17][C:16]([NH:19][C:20]([C:22]3[CH:36]=[CH:35][C:25]([O:26][CH2:27][C:28]([OH:30])=[O:29])=[CH:24][CH:23]=3)=[O:21])=[CH:15][CH:14]=2)[CH2:11][CH2:12][NH:7][CH2:8][CH2:9]1

Participants

3

Reactant 1

HCID 53850602Tert-butyl 4-(4-(4-(1,1-dimethylethoxycarbonyl)piperazin-1-yl)phenylaminocarbonyl)phenoxyacetate

Product 1

HCID 540829364-(4-(Piperazin-1-yl)phenylaminocarbonyl)phenoxyacetic acidYield 40.4%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

To a 100 mL round bottomed flask with a stirring bar and a gas dispersion tube was added tert-butyl 4-(4-(4-(1,1-dimethylethoxycarbonyl)piperazin-1-yl)phenylaminocarbonyl)phenoxyacetate (0.78 g, 1.52 mmol) and EtOAc (40 mL). This solution was cooled in an ice bath and HCl gas was sparged through the solution for 15 min. The resulting mixture was aged 90 min. The excess HCl and EtOAc were removed in vacuo and the crude product was purified by preparative reverse phase HPLC. There was obtained 0.218 g of 4-(4-(piperazin-1-yl)phenylaminocarbonyl)phenoxyacetic acid as a crystalline solid.

Workup

  1. temperatureThis solution was cooled in an ice bath
  2. customHCl gas was sparged through the solution for 15 min
  3. customThe excess HCl and EtOAc were removed in vacuo
  4. customthe crude product was purified by preparative reverse phase HPLC

Sources & evidence

ORD record
ord-0c649915052b432592e80879a007e83e
Source dataset
uspto-grants-1998_12
Patent number
US05854245

Reaction notes

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