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

HRID 264292Notes

Reaction equation

HRID 264292 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-5465665d44c34f55a80bbc303dbfa081
Source dataset
uspto-grants-1997_07
Patent number
US05646167

Reaction notes

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