Methyl bromoacetate → HCID 66603443, compound

HRID 751008Notes

Reaction equation

HRID 751008 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([CH:9]=[CH:10][CH:11]=1)[C:5]([O:7][CH3:8])=[O:6].Br[CH2:13][C:14]([O:16]C)=[O:15].[C:18]([O-])(=O)C.[Na+]>CO>[CH3:18][N:1]([C:2]1[CH:11]=[CH:10][CH:9]=[C:4]([C:5]([O:7][CH3:8])=[O:6])[CH:3]=1)[CH2:13][C:14]([OH:16])=[O:15]

Participants

5

Reactant 3

HCID 60984Methyl bromoacetateHCID 78274Benzoic acid, 3-amino-, methyl esterHCID 517045Sodium Acetate

Product 1

HCID 66603443HCID 66603443, compoundYield 45%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of methyl 3-aminobenzoate (4.00 g, 26.5 mmol), methyl bromoacetate (4.05 g, 26.5 mmol) and sodium acetate (1.1 eq.) in methanol (30 mL) was stirred at ambient temperature for 48 h. The resulting white precipitate was collected by filtration, washed with a small amount of methanol, and dried under vacuum to afford methyl-N-(3-carbomethoxyphenyl)glycine (2.69 g, 12.1 mmol, 45%). 1H NMR (CDCl3, 300 MHz): δ 7.41 (1H, d, J=8 Hz), 7.28-7.20 (2H, m), 6.79 (1H, d, J=8 Hz), 4.43 (1H, br), 3.97 (2H, s), 3.90 (3H, s), 3.80 (3H, s).

Workup

  1. filtrationThe resulting white precipitate was collected by filtration
  2. washwashed with a small amount of methanol
  3. customdried under vacuum

Sources & evidence

ORD record
ord-8d659217834542dab151afaeb35c401c
Source dataset
uspto-grants-2008_07
Patent number
US07405233B2

Reaction notes

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