Dimethylformamide → Ethyl 2-(4-{[(tert-butoxy)carbonyl]amino}phenoxy)acetate

HRID 1459421Notes

Reaction equation

HRID 1459421 reaction equation
[CH3:1][C:2]([CH3:15])([O:4][C:5]([NH:7][C:8]1[CH:13]=[CH:12][C:11]([OH:14])=[CH:10][CH:9]=1)=[O:6])[CH3:3].C([O-])([O-])=O.[Cs+].[Cs+].CN(C=O)C.Br[CH2:28][C:29]([O:31][CH2:32][CH3:33])=[O:30]>C(Cl)(Cl)Cl>[CH3:3][C:2]([CH3:15])([O:4][C:5]([NH:7][C:8]1[CH:9]=[CH:10][C:11]([O:14][CH2:28][C:29]([O:31][CH2:32][CH3:33])=[O:30])=[CH:12][CH:13]=1)=[O:6])[CH3:1]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 7748Ethyl bromoacetateHCID 10796Cesium carbonateHCID 2756771N-Boc-4-hydroxyaniline

Product 1

HCID 54043329Ethyl 2-(4-{[(tert-butoxy)carbonyl]amino}phenoxy)acetateYield 102.8%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

To a 500 mL round bottomed flask with a stirring bar and an argon inlet was added 4-(1,1-dimethylethoxycarbonylamino)phenol (8.20 g, 39.19 mmol), Cs2CO3 (25.54 g, 78.38 mmol), DMF (75 mL), and ethyl bromoacetate (4.78 mL, 43.11 mmol). This heterogeneous mixture was stirred at ambient temperature for 3.5 h. The mixture was diluted with a little CHCl3 and filtered through a frit to remove the salts. The DMF was removed under high vacuum and the residue was suspended in 500 mL of EtOAc. This mixture was washed with H2O (3×), and brine. Drying (MgSO4), filtration and removal of the solvent in vacuo, gave an oil. This material was chromatographed on 400 g of silica gel using 20% EtOAc-hexane as eluant. There was obtained 11.9 g (100%) of ethyl (4-(1,1-dimethylethoxycarbonylamino)phenoxy)acetate as an oil.

Workup

  1. filtrationfiltered through a frit
  2. customto remove the salts
  3. customThe DMF was removed under high vacuum
  4. washThis mixture was washed with H2O (3×), and brine
  5. customDrying
  6. filtration(MgSO4), filtration and removal of the solvent in vacuo
  7. customgave an oil
  8. customThis material was chromatographed on 400 g of silica gel using 20% EtOAc-hexane as eluant

Sources & evidence

ORD record
ord-6033d6da4ae74af690ac9f3eda8e2847
Source dataset
uspto-grants-1998_12
Patent number
US05854245

Reaction notes

Loading…