2-Nitrobenzaldehyde → 2-(2-Nitrobenzylamino)succinic acid dimethyl ester

HRID 1791128Notes

Reaction equation

HRID 1791128 reaction equation
Cl.[CH3:2][O:3][C:4](=[O:12])[C@@H:5]([CH2:7][C:8]([O:10][CH3:11])=[O:9])[NH2:6].C([O-])(=O)C.[Na+].[N+:18]([C:21]1[CH:28]=[CH:27][CH:26]=[CH:25][C:22]=1[CH:23]=O)([O-:20])=[O:19].C([BH3-])#N.[Na+]>C(O)C>[CH3:2][O:3][C:4](=[O:12])[CH:5]([NH:6][CH2:23][C:22]1[CH:25]=[CH:26][CH:27]=[CH:28][C:21]=1[N+:18]([O-:20])=[O:19])[CH2:7][C:8]([O:10][CH3:11])=[O:9]

Participants

6

Reactant 4

HCID 111012-NitrobenzaldehydeHCID 517045Sodium AcetateHCID 5003444Sodium cyanoborohydrideHCID 510515941,4-dimethyl (2R)-2-aminobutanedioate hydrochloride

Product 1

HCID 235355542-(2-Nitrobenzylamino)succinic acid dimethyl esterYield 99%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of D-aspartic acid dimethyl ester hydrochloride (4.2 g, 21.25 mmol) and sodium acetate (1.46 g, 17.85 mmol) was stirred in 25 mL of warm ethanol for 10 min. 2-Nitrobenzaldehyde (1.35 g, 8.936 mmol) was added and stirring was continued at room temperature for 1.5 h. Sodium cyanoborohydride (333.88 mg, 5.31 mmol) was added in portions over 5 min. and stirring at room temperature continued overnight. The reaction mixture was concentrated in vacuo, the residue was diluted with ethyl acetate and washed with saturated aqueous sodium bicarbonate and sodium chloride solutions. The organic layer was dried (Na2SO4) and concentrated to give 2.62 g of the title compound as a light brown oil.

Workup

  1. stirringstirring at room temperature
  2. waitcontinued overnight
  3. concentrationThe reaction mixture was concentrated in vacuo
  4. additionthe residue was diluted with ethyl acetate
  5. washwashed with saturated aqueous sodium bicarbonate and sodium chloride solutions
  6. dry with materialThe organic layer was dried (Na2SO4)
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-7720740d4fb445fe92169049cc1dcd51
Source dataset
uspto-grants-2006_07
Patent number
US07074783B2

Reaction notes

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