Acetaldehyde → 2-[N-(Methylmethylene)amino]-4methylpentanoic acid, tert-butyl ester

HRID 854341Notes

Reaction equation

HRID 854341 reaction equation
[C:1]([O:5][C:6](=[O:13])[C@H:7]([CH2:9][CH:10]([CH3:12])[CH3:11])[NH2:8])([CH3:4])([CH3:3])[CH3:2].[CH:14](=O)[CH3:15].S([O-])([O-])(=O)=O.[Na+].[Na+]>>[CH3:14][CH:15]=[N:8][CH:7]([CH2:9][CH:10]([CH3:11])[CH3:12])[C:6]([O:5][C:1]([CH3:4])([CH3:3])[CH3:2])=[O:13]

Participants

4

Reactant 3

HCID 177AcetaldehydeHCID 24436Sodium SulfateHCID 7022311tert-butyl (2S)-2-amino-4-methylpentanoate

Product 1

HCID 589340072-[N-(Methylmethylene)amino]-4methylpentanoic acid, tert-butyl ester

Procedure

A solution of leucine tert-butyl ester (2.0 g, 8.9 mmol) and acetaldehyde (999 ul, 17.9 mmol) was stirred at room temperature for 5 minutes. Anhydrous sodium sulphate was added and the mixture stirred at room temperature for 18 hours. The solid was removed by filtration and the solvent evaporated in vacuo to afford the title compound as an oil.

Workup

  1. customThe solid was removed by filtration
  2. customthe solvent evaporated in vacuo

Sources & evidence

ORD record
ord-948466db67134022aee4612d43eca131
Source dataset
uspto-grants-2007_08
Patent number
US07259163B2

Reaction notes

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