Benzaldehyde → Tert-butyl N-benzylidenealaninate

HRID 1957024Notes

Reaction equation

HRID 1957024 reaction equation
Cl.[C:2]([O:6][C:7](=[O:11])[C@H:8]([CH3:10])[NH2:9])([CH3:5])([CH3:4])[CH3:3].C(N(CC)CC)C.S([O-])([O-])(=O)=O.[Mg+2].[CH:25](=O)[C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1>C(Cl)Cl.O.[Cl-].[Na+].O>[C:2]([O:6][C:7](=[O:11])[C@H:8]([CH3:10])[N:9]=[CH:25][C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1)([CH3:5])([CH3:4])[CH3:3]

Participants

8

Reactant 4

HCID 240BenzaldehydeHCID 8471TriethylamineHCID 24083Sulfuric acid magnesium salt (1:1)HCID 11275390tert-Butyl alaninate hydrochloride

Product 1

HCID 13433755Tert-butyl N-benzylidenealaninate

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6344DichloromethaneSolventHCID 57417360Sodium chloride; waterSolvent

Procedure

To a stirred solution of L-alanine t-butyl ester hydrochloride (1.03 g, 5.69 mmol), triethylamine (0.792 ml, 5.69 mmol) and magnesium sulfate (463 mg) in methylene chloride (11 ml) is added benzaldehyde (0.549 ml, 5.40 mmol) at room temperature under nitrogen atmosphere. The reaction mixture is stirred at room temperature for 17 hours, then diluted with water (10 ml), and brine, successively, and dried over magnesium sulfate and concentrated in vacuo to give N-(phenylmethylene)alanine t-butyl ester as a colorless oil.

Workup

  1. dry with materialsuccessively, and dried over magnesium sulfate
  2. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-4412b51422a04e1e8db101f9c54fd94a
Source dataset
uspto-grants-1998_07
Patent number
US05780498

Reaction notes

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