4-Methoxybenzenesulfonyl chloride → N-[4-methoxybenzenesulfonyl]-alanine methyl ester

HRID 1720587Notes

Reaction equation

HRID 1720587 reaction equation
Cl.[CH3:2][O:3][C:4](=[O:8])[C@H:5]([CH3:7])[NH2:6].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.[OH-].[Na+]>C(Cl)Cl>[CH3:2][O:3][C:4](=[O:8])[C@H:5]([CH3:7])[NH:6][S:24]([C:21]1[CH:20]=[CH:19][C:18]([O:17][CH3:16])=[CH:23][CH:22]=1)(=[O:26])=[O:25]

Participants

6

Reactant 4

HCID 74014-Methoxybenzenesulfonyl chlorideHCID 8471TriethylamineHCID 14798Sodium HydroxideHCID 2733257Alanine methyl ester hydrochloride

Product 1

HCID 7081982N-[4-methoxybenzenesulfonyl]-alanine methyl ester

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Alanine methyl ester hydrochloride (7.0 g, 50.0 mmol) is dissolved in methylene chloride (100.0 mL) and triethylamine (20.0 mL, 143.0 mmol). To this solution is added 4-methoxybenzenesulfonyl chloride (10.3 g, 50.0 mmol), and the reaction is stirred at room temperature briefly. The reaction is made basic with 1N sodium hydroxide, and washed with methylene chloride. The combined organic layers are dried (Na2SO4), and the solvent is evaporated. Hexane is added to the residue and the precipitate is collected to give N-[4-methoxybenzenesulfonyl]-alanine methyl ester.

Workup

  1. washwashed with methylene chloride
  2. dry with materialThe combined organic layers are dried (Na2SO4)
  3. customthe solvent is evaporated
  4. additionHexane is added to the residue
  5. customthe precipitate is collected

Sources & evidence

ORD record
ord-7ebbe66aebb04a53b2d5ddf9183a29cf
Source dataset
uspto-grants-1996_04
Patent number
US05506242

Reaction notes

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