Cesium carbonate → 4-(1,1-Dimethylethoxycarbonyl)amino-3-methylphenoxyacetamide

HRID 1584128Notes

Reaction equation

HRID 1584128 reaction equation
[CH3:1][C:2]([CH3:16])([O:4][C:5]([NH:7][C:8]1[CH:13]=[CH:12][C:11]([OH:14])=[CH:10][C:9]=1[CH3:15])=[O:6])[CH3:3].C([O-])([O-])=O.[Cs+].[Cs+].Br[CH2:24][C:25]([NH2:27])=[O:26]>CN(C=O)C>[CH3:3][C:2]([CH3:16])([O:4][C:5]([NH:7][C:8]1[CH:13]=[CH:12][C:11]([O:14][CH2:24][C:25]([NH2:27])=[O:26])=[CH:10][C:9]=1[CH3:15])=[O:6])[CH3:1]

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 696322-BromoacetamideHCID 15429162tert-Butyl (4-hydroxy-2-methylphenyl)carbamate

Product 1

HCID 158708024-(1,1-Dimethylethoxycarbonyl)amino-3-methylphenoxyacetamideYield 78.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a 200 mL round bottomed flask with a stirring bar, and an argon inlet was added 4-(1,1-dimethylethoxycarbonyl)amino-3-methylphenol (5.00 g, 22.39 mmot), Cs2CO3 (14.59 g, 44.78 mmol), DMF (50 mL), and bromoacetamide (3.24 g, 23.51 mmol). This mixture was stirred vigorously at ambient temperature for 24 h. The mixture was filtered through a frit and the DMF was removed under high vacuum. The residue was dissolved in EtOAc (300 mL) and washed wit H2O (2×) and brine (1×). Drying (MgSO4), filtration, and removal of the solvent in vacuo gave a solid. This material was triturated with EtOAc, the solid was collected by filtration and dried in vacuo to give 4.91 g (78%) of 4-(1,1-dimethyl-ethoxycarbonyl)amino-3-methylphenoxyacetamide as a white, crystalline solid.

Workup

  1. filtrationThe mixture was filtered through a frit
  2. customthe DMF was removed under high vacuum
  3. dissolutionThe residue was dissolved in EtOAc (300 mL)
  4. washwashed wit H2O (2×) and brine (1×)
  5. customDrying
  6. filtration(MgSO4), filtration, and removal of the solvent in vacuo
  7. customgave a solid
  8. customThis material was triturated with EtOAc
  9. filtrationthe solid was collected by filtration
  10. customdried in vacuo

Sources & evidence

ORD record
ord-6a23bcd563d64b39b11005478893950e
Source dataset
uspto-grants-1999_08
Patent number
US05932582

Reaction notes

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