4-Methoxybenzenesulfonyl chloride → N-[4-methoxybenzenesulfonyl]-(D)-asparagine

HRID 264323Notes

Reaction equation

HRID 264323 reaction equation
[NH2:1][C@@H:2]([C:7]([OH:9])=[O:8])[CH2:3][C:4](=[O:6])[NH2:5].C(N(CC)CC)C.[CH3:17][O:18][C:19]1[CH:24]=[CH:23][C:22]([S:25](Cl)(=[O:27])=[O:26])=[CH:21][CH:20]=1>O1CCOCC1.O>[CH3:17][O:18][C:19]1[CH:20]=[CH:21][C:22]([S:25]([NH:1][C@@H:2]([C:7]([OH:9])=[O:8])[CH2:3][C:4](=[O:6])[NH2:5])(=[O:27])=[O:26])=[CH:23][CH:24]=1

Participants

6

Reactant 3

HCID 74014-Methoxybenzenesulfonyl chlorideHCID 8471TriethylamineHCID 439600D-Asparagine

Product 1

HCID 27014145N-[4-methoxybenzenesulfonyl]-(D)-asparagine

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
0 °C

Procedure

D-asparagine (13.2 g, 100.0 mmol) is dissolved in dioxane (75.0 mL) and water (125.0 mL), triethylamine (21.0 mL, 150.0 mmol) is added, and the solution is cooled to 0° C. To this solution is added 4-methoxybenzenesulfonyl chloride (22.7 g, 110.0 mmol) over 10 minutes. The reaction is warmed to room temperature and stirred for 3 days. The precipitate is then filtered off, the filtrate is acidified to pH=~4, and extracted well with ethyl acetate. A first crop of pure product precipitates from the ethyl acetate and is collected by filtration. A second crop is obtained by evaporating off the ethyl acetate, and rinsing the solid obtained with water to remove inorganic salts. The two crops are combined to give N-[4-methoxybenzenesulfonyl]-(D)-asparagine.

Workup

  1. temperatureThe reaction is warmed to room temperature
  2. filtrationThe precipitate is then filtered off
  3. extractionextracted well with ethyl acetate
  4. customA first crop of pure product precipitates from the ethyl acetate
  5. filtrationis collected by filtration
  6. customA second crop is obtained
  7. customby evaporating off the ethyl acetate
  8. washrinsing the solid
  9. customobtained with water
  10. customto remove inorganic salts

Sources & evidence

ORD record
ord-44ac81cfc7a143c2b1ca49766096e529
Source dataset
uspto-grants-1997_07
Patent number
US05646167

Reaction notes

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