4-Methoxybenzenesulfonyl chloride → HCID 3113410, compound

HRID 742049Notes

Reaction equation

HRID 742049 reaction equation
Cl.[CH2:2]([O:4][C:5](=[O:8])[CH2:6][NH2:7])[CH3:3].C(N(CC)CC)C.[CH3:16][O:17][C:18]1[CH:23]=[CH:22][C:21]([S:24](Cl)(=[O:26])=[O:25])=[CH:20][CH:19]=1>O1CCOCC1.O>[CH3:16][O:17][C:18]1[CH:19]=[CH:20][C:21]([S:24]([NH:7][CH2:6][C:5]([O:4][CH2:2][CH3:3])=[O:8])(=[O:26])=[O:25])=[CH:22][CH:23]=1

Participants

6

Reactant 3

HCID 74014-Methoxybenzenesulfonyl chlorideHCID 8471TriethylamineHCID 2723640Glycine ethyl ester, hydrochloride

Product 1

HCID 3113410HCID 3113410, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
0 °C

Procedure

Glycine ethyl ester hydrochloride (31.39 g, 225.0 mmol) is dissolved in dioxane (150 mL) and water (150 mL), triethylamine (69.0 mL, 495.0 mmol) is added, and the solution is cooled to 0° C. To this solution is added 4-methoxybenzenesulfonyl chloride (51.15 g, 248.0 mmol) over 10 minutes. The reaction is warmed to room temperature and stirred overnight. The next day the mixture is reduced to one-half volume by evaporating solvent, diluted with 1N sodium hydroxide, and extracted well with ether. The combined organic layers are washed with brine, dried (Na2SO4), and the solvent is evaporated. The product is recrystallized from ether/ethyl acetate/hexanes to give ethyl 2-[[4-methoxybenzenesulfonyl]amino]acetate.

Workup

  1. temperatureThe reaction is warmed to room temperature
  2. customby evaporating solvent
  3. additiondiluted with 1N sodium hydroxide
  4. extractionextracted well with ether
  5. washThe combined organic layers are washed with brine
  6. dry with materialdried (Na2SO4)
  7. customthe solvent is evaporated
  8. customThe product is recrystallized from ether/ethyl acetate/hexanes

Sources & evidence

ORD record
ord-9d72ea1824904a9baaea46182f13b4ca
Source dataset
uspto-grants-1996_09
Patent number
US05552419

Reaction notes

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