Hydrochloric Acid → L-Aspartic acid diethyl ester hydrochloride

HRID 993476Notes

Reaction equation

HRID 993476 reaction equation
[C:1]([Cl:4])(=O)[CH3:2].Cl.[NH2:6][C@H:7]([C:12]([OH:14])=[O:13])[CH2:8][C:9]([OH:11])=[O:10].[CH2:15](O)[CH3:16]>>[ClH:4].[NH2:6][C@H:7]([C:12]([O:14][CH2:1][CH3:2])=[O:13])[CH2:8][C:9]([O:11][CH2:15][CH3:16])=[O:10]

Participants

5

Reactant 4

HCID 313Hydrochloric AcidHCID 702EthanolHCID 5960L-Aspartic AcidHCID 6367Acetyl chloride

Product 1

HCID 12416466L-Aspartic acid diethyl ester hydrochloride

Conditions

Temperature
25 °C

Procedure

Absolute ethanol (420 ml) was cooled in ice and acetyl chloride (71.4 ml, 1.03 mol) was added dropwise to generate HCl in situ. After the addition, the reaction was stirred for additional 30 minutes. L-Aspartic acid (33.27 g, 0.25 mol) was added in one portion and the solution heated slowly after dissolution to reflux. Refluxing was continued until the reaction was complete (TLC). The reaction mixture was then cooled to 25° C. and the solvent was removed under reduced pressure. Further drying under vacuum gave crude diethyl L-aspartate hydrochloride 2 as a viscous oil which crystallised on standing to a white solid, yield: 60 g (100%). This material was used without further purification. Spectral data for this sample were consistent with those given in the literature1. 13C NMR (75 MHz, d6-DMSO) 169.1, 168.2, 70.0, 60.9, 48.5, 34.2, 14.9 and 13.9.

Workup

  1. additionAfter the addition
  2. temperaturethe solution heated slowly
  3. dissolutionafter dissolution
  4. temperatureto reflux
  5. temperatureRefluxing
  6. customthe solvent was removed under reduced pressure
  7. customFurther drying under vacuum

Sources & evidence

ORD record
ord-a56a4f74157f44afb6d28328400b8104
Source dataset
uspto-grants-2002_10
Patent number
US06472533B1

Reaction notes

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