4-Methoxybenzenesulfonyl chloride → L-Aspartic Acid

HRID 324288

Reaction equation

HRID 324288 reaction equation
[NH2:1][C@@H:2]([C:7]([OH:9])=[O:8])[CH2:3][C:4]([OH:6])=[O:5].COC1C=CC(S(Cl)(=O)=O)=CC=1>[OH-].[Na+]>[NH2:1][C@H:2]([C:7]([OH:9])=[O:8])[CH2:3][C:4]([OH:6])=[O:5]

Participants

4

Reactant 2

HCID 74014-Methoxybenzenesulfonyl chlorideHCID 83887D-Aspartic Acid

Product 1

HCID 5960L-Aspartic Acid

Reagents, catalysts & solvents 1

HCID 14798Sodium HydroxideSolvent

Conditions

Temperature
70 °C

Procedure

D-Aspartic acid (2.66 g) is suspended in 2N NaOH (30 mL) and 4-methoxyphenylsulfonyl chloride (4.12 g) is added. The mixture is stirred at 70° C. for 5 hours (clear solution), cooled down to room temperature and extracted with methylene chloride. The aqueous phase, after acidifying with 12N HCl, is extracted with ethyl acetate. The combined organic phases are with brine, dried (Na2SO4) and concentrated under reduced pressure to give N-[4-methoxyphenyl)sulfonyl]-D-aspartic acid as a white solid.

Workup

  1. temperaturecooled down to room temperature
  2. extractionextracted with methylene chloride
  3. extractionis extracted with ethyl acetate
  4. dry with materialdried (Na2SO4)
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-de226369a28f4cc8b18b16c2cda762da
Source dataset
uspto-grants-2001_04
Patent number
US06218389B1

Linked notes

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