4-(1,1-Dimethylethoxycarbonyl)amino-3-methylphenoxyacetamide → 2-(4-Amino-3-methylphenoxy)acetamide
Reaction equation
CC(C)(OC([NH:7][C:8]1[CH:18]=[CH:17][C:11]([O:12][CH2:13][C:14]([NH2:16])=[O:15])=[CH:10][C:9]=1[CH3:19])=O)C>FC(F)(F)C(O)=O>[NH2:7][C:8]1[CH:18]=[CH:17][C:11]([O:12][CH2:13][C:14]([NH2:16])=[O:15])=[CH:10][C:9]=1[CH3:19]Participants
3
Reactant 1
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 0 °C
Procedure
To a 200 m1L round bottomed flask with a stirring bar and an argon inlet was added 4-(1,1-dimethylethoxycarbonyl)amino-3-methylphenoxyacetamide (4.91 g, 17.52 mmol) and trifluoroacetic acid (50 mL). This solution was stirred at 0° C. for 5 h. The trifluoroacetic acid was removed in vacuo and the residue was partitioned between EtOAc and aqueous NaHCO3 solution. The layers were separated and the organic phase was washed with brine, dried (MgSO4), filtered and concentrated in vacuo to give 1.60 g of 4-amino-3-methylphenoxy-acetamide as a white solid.
Workup
- customThe trifluoroacetic acid was removed in vacuo
- customthe residue was partitioned between EtOAc and aqueous NaHCO3 solution
- customThe layers were separated
- washthe organic phase was washed with brine
- dry with materialdried (MgSO4)
- filtrationfiltered
- concentrationconcentrated in vacuo
Sources & evidence
- ORD record
- ord-b35967b5bea747a38905af3f99a52b10
- Source dataset
- uspto-grants-1999_08
- Patent number
- US05932582
Reaction notes
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