Sodium Iodide → Ethyl N-(4-chlorobenzyl)-N-phenylglycinate

HRID 2184079Notes

Reaction equation

HRID 2184079 reaction equation
[CH2:1]([O:3][C:4](=[O:13])[CH2:5][NH:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)[CH3:2].[Cl:14][C:15]1[CH:22]=[CH:21][C:18]([CH2:19]Cl)=[CH:17][CH:16]=1.[I-].[Na+]>C1(C)C=CC=CC=1.C(OCC)(=O)C>[Cl:14][C:15]1[CH:22]=[CH:21][C:18]([CH2:19][N:6]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)[CH2:5][C:4]([O:3][CH2:1][CH3:2])=[O:13])=[CH:17][CH:16]=1

Participants

6

Reactant 3

HCID 5238Sodium IodideHCID 77231-Chloro-4-(chloromethyl)benzeneHCID 75190N-Phenylglycine ethyl ester

Product 1

HCID 22475636Ethyl N-(4-chlorobenzyl)-N-phenylglycinateYield 51.2%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
80 °C

Procedure

N-phenylglycine ethyl ester (781 mg, 4.3 mmol), 4-chlorobenzyl chloride (690 mg, 4.3 mmol) and sodium iodide (64 mg) were dissolved in toluene (7 mL) under argon. The reaction was heated in a graphite bath at 80° C. for 24 h. After cooling to room temperature, the reaction was diluted with ethyl acetate and washed with 1M HCl followed by brine. The solution was dried over MgSO4, filtered, and concentrated in vacuo. Purification of the resultant oil by flash chromatography (10:1 hexanes/EtOAc) afforded the title compound as a green oil (669 mg, 51%). MS (ES+) m/z 304 (MH+).

Workup

  1. temperatureAfter cooling to room temperature
  2. washwashed with 1M HCl
  3. dry with materialThe solution was dried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customPurification of the resultant oil by flash chromatography (10:1 hexanes/EtOAc)

Sources & evidence

ORD record
ord-4b1bf8a114e04ec69b30e81acc4cee70
Source dataset
uspto-grants-2005_05
Patent number
US06900244B2

Reaction notes

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