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

HRID 2187985Notes

Reaction equation

HRID 2187985 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 di-chloromethane 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-66560178f7fd4a518b2bbacf4750ca49
Source dataset
uspto-grants-2002_06
Patent number
US06410580B1

Reaction notes

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