L-Aspartic acid diethyl ester hydrochloride → 1,4-Dimethyl L-aspartate

HRID 1885417Notes

Reaction equation

HRID 1885417 reaction equation
Cl.[CH2:2]([O:4][C:5](=[O:14])[C@H:6]([CH2:8][C:9]([O:11][CH2:12]C)=[O:10])[NH2:7])C>C(=O)([O-])[O-].[Na+].[Na+]>[NH2:7][C@H:6]([C:5]([O:4][CH3:2])=[O:14])[CH2:8][C:9]([O:11][CH3:12])=[O:10]

Participants

3

Reactant 1

HCID 12416466L-Aspartic acid diethyl ester hydrochloride

Product 1

HCID 1112071,4-Dimethyl L-aspartateYield 84.3%

Reagents, catalysts & solvents 1

HCID 10340Sodium CarbonateSolvent

Procedure

Diethylaspartate hydrochloride (3, 85.31 g, 0.432 mol) was dissolved in a saturated solution of aqueous sodium carbonate (200 mL) and extracted with ethyl acetate (10×250 mL) in a separatory funnel. The combined organic phases were dried by filtration through magnesium sulfate and sodium sulfate and concentrated in vacuo to provide dimethyl aspartate (58.73 g, 0.364 mol, 84%) as a pale yellow oil. This material provided satisfactory 1H NMR data and was used immediately in the preparation of N-benzyloxycarbonylglycyl-L-α-aspartic acid dimethyl ester (5).

Workup

  1. extractionextracted with ethyl acetate (10×250 mL) in a separatory funnel
  2. dry with materialThe combined organic phases were dried by filtration through magnesium sulfate and sodium sulfate
  3. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-a0f6b6fcd7e244e89c1dbf6460731807
Source dataset
uspto-grants-1992_09
Patent number
US05144073

Reaction notes

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