Potassium Carbonate → Methyl 2-{[(4-bromophenyl)methyl]amino}acetate
Reaction equation
[Br:1][C:2]1[CH:9]=[CH:8][C:5]([CH2:6]Br)=[CH:4][CH:3]=1.Cl.[CH3:11][O:12][C:13](=[O:16])[CH2:14][NH2:15].C(=O)([O-])[O-].[K+].[K+]>C1COCC1.O.S([O-])([O-])(=O)=O.C([N+](CCCC)(CCCC)CCCC)CCC.C([N+](CCCC)(CCCC)CCCC)CCC>[CH3:11][O:12][C:13](=[O:16])[CH2:14][NH:15][CH2:6][C:5]1[CH:8]=[CH:9][C:2]([Br:1])=[CH:3][CH:4]=1Participants
7
Reactant 3
Product 1
Reagents, catalysts & solvents 3
Conditions
- Temperature
- 40 °C
Procedure
i)—To a solution of p-bromobenzyl bromide (10 g, 40 mmol) in THF (100 ml) and water (7.2 ml) were added glycine methyl ester hydrochloride (10 g, 80 mmol), potassium carbonate (22.1 g, 160 mmol) and tetrabutylammonium sulfate (136 mg, 0.4 mmol). After 1 h stirring at 40° C., the reaction mixture was poured in water and the product was extracted into ethyl acetate. The combined organic phases were washed with brine, dried over magnesium sulfate and concentrated under reduced pressure. Column chromatography afforded (4-bromo-benzylamino)acetic acid methyl ester (6.4 g) as a colorless oil.
Workup
- extractionthe product was extracted into ethyl acetate
- washThe combined organic phases were washed with brine
- dry with materialdried over magnesium sulfate
- concentrationconcentrated under reduced pressure
Sources & evidence
- ORD record
- ord-5876c10b13fe4b6dbd63ce67472044e7
- Source dataset
- uspto-grants-2011_06
- Patent number
- US07960560B2
Reaction notes
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