Potassium Carbonate → N-(4-iodobenzyl)glycine tert-butyl ester

HRID 2183531Notes

Reaction equation

HRID 2183531 reaction equation
[I:1][C:2]1[CH:9]=[CH:8][C:5]([CH2:6][NH2:7])=[CH:4][CH:3]=1.[C:10]([O:14][C:15](=[O:18])[CH2:16]Br)([CH3:13])([CH3:12])[CH3:11].C(=O)([O-])[O-].[K+].[K+]>C1(C)C=CC=CC=1.O>[C:10]([O:14][C:15](=[O:18])[CH2:16][NH:7][CH2:6][C:5]1[CH:8]=[CH:9][C:2]([I:1])=[CH:3][CH:4]=1)([CH3:13])([CH3:12])[CH3:11]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 79177tert-Butyl bromoacetateHCID 27375334-Iodobenzylamine

Product 1

HCID 22473408N-(4-iodobenzyl)glycine tert-butyl esterYield 31%

Reagents, catalysts & solvents 1

HCID 22272177Toluene waterSolvent

Procedure

A mixture of 4-iodobenzylamine (5.0 g, 21.5 mmol), tert-butylbromoacetate (4.19 g, 21.5 mmol), potassium carbonate (3.55 g, 21.5 mmol) in 40 mL of 1:1 toluene/water was stirred at room temperature for 16 h. The reaction mixture was extracted with ethyl acetate (100 mL×3) and the combined organic phase was washed with brine, dried over sodium sulfate, and evaporated to give an oil. Chromatography on silica gel gave 2.3 g (31%) of N-(4-iodobenzyl)glycine tert-butyl ester as a colorless oil.

Workup

  1. extractionThe reaction mixture was extracted with ethyl acetate (100 mL×3)
  2. washthe combined organic phase was washed with brine
  3. dry with materialdried over sodium sulfate
  4. customevaporated
  5. customto give an oil

Sources & evidence

ORD record
ord-7eb1e0f467c5417fbd0c7c90b52d3e89
Source dataset
uspto-grants-2005_05
Patent number
US06900213B2

Reaction notes

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