Benzophenone imine → N-(Diphenylmethylene)glycine tert-butyl ester

HRID 651333Notes

Reaction equation

HRID 651333 reaction equation
Cl.[C:2]([O:6][C:7](=[O:10])[CH2:8][NH2:9])([CH3:5])([CH3:4])[CH3:3].[C:11](=N)([C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1>ClCCl>[C:2]([O:6][C:7](=[O:10])[CH2:8][N:9]=[C:11]([C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)([CH3:5])([CH3:4])[CH3:3]

Participants

4

Reactant 2

HCID 136809Benzophenone imineHCID 2725036Glycine tert-butyl ester hydrochloride

Product 1

HCID 688171N-(Diphenylmethylene)glycine tert-butyl esterYield 91.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of glycine t-butyl ester hydrochloride (10 g, 59.65 mmol) in 250 mL of dichloromethane is treated with benzophenoneimine (10.8 g, 59.6 mmol) at RT. After 16 h, the mixture is washed with brine, dried over anhydrous MgSO4 and concentrated to give benzhydrylideneaminoacetic acid t-butyl ester as a white solid (16.1 g, 91%).

Workup

  1. washthe mixture is washed with brine
  2. dry with materialdried over anhydrous MgSO4
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-fdab95d414784f04b65969e3f31479ce
Source dataset
uspto-grants-2001_08
Patent number
US06277987B1

Reaction notes

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