Lithium Hydroxide → N-[(4-Bromophenyl)methyl]glycine

HRID 915823Notes

Reaction equation

HRID 915823 reaction equation
C[O:2][C:3](=[O:14])[CH2:4][NH:5][CH2:6][C:7]1[CH:12]=[CH:11][C:10]([Br:13])=[CH:9][CH:8]=1.[OH-].[Li+]>O>[Br:13][C:10]1[CH:9]=[CH:8][C:7]([CH2:6][NH:5][CH2:4][C:3]([OH:14])=[O:2])=[CH:12][CH:11]=1

Participants

4

Reactant 2

HCID 3939Lithium HydroxideHCID 28431396Methyl 2-{[(4-bromophenyl)methyl]amino}acetate

Product 1

HCID 28354373N-[(4-Bromophenyl)methyl]glycine

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To (4-bromo-benzylamino)-acetic acid methyl ester (100 mg, 0.342 mmol) in water (3 mL) was added lithium hydroxide (57 mg, 0.684 mmol). After 4 hours the solution was partially quenched with 1 M HCl (1.5 mL) to give a solution pH of ca 8.5. The pH of the solution was carefully adjusted to pH 5 by the addition of 3-4 drops of 1 M HCl. Stirring overnight yielded a white precipitate. This was isolated via filtration, rinsing with a small amount of cold water, to give the desired zwitterion.

Workup

  1. customAfter 4 hours the solution was partially quenched with 1 M HCl (1.5 mL)

Sources & evidence

ORD record
ord-172b8494d81840aabcac1ed3fc16744a
Source dataset
uspto-grants-2007_09
Patent number
US07268142B2

Reaction notes

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