4-Methoxybenzenesulfonyl chloride → (2R)-2-{[(4-methoxyphenyl)sulfonyl]amino}-4-methylpentanoic acid

HRID 1720580

Reaction equation

HRID 1720580 reaction equation
[NH2:1][C@@H:2]([C:7]([OH:9])=[O:8])[CH2:3][CH:4]([CH3:6])[CH3:5].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.C(Cl)Cl>[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][CH:4]([CH3:6])[CH3:5])(=[O:27])=[O:26])=[CH:23][CH:24]=1

Participants

7

Reactant 3

HCID 74014-Methoxybenzenesulfonyl chlorideHCID 8471TriethylamineHCID 439524D-Leucine

Product 1

HCID 744873(2R)-2-{[(4-methoxyphenyl)sulfonyl]amino}-4-methylpentanoic acid

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6344DichloromethaneSolventHCID 312751,4-DioxaneSolvent

Procedure

(D)-leucine (7.1 g, 53.9 mmol) is dissolved in dioxane (60.0 mL) and water (60.0 mL). To this solution is added triethylamine (11.3 mL, 80.9 mmol) and 4-methoxybenzenesulfonyl chloride (12.25 g, 59.3 mmol), and the reaction is stirred at room temperature overnight. The reaction is then diluted with methylene chloride and washed successively with 2.5N hydrochloric acid, water, and brine. The organic phase is dried (Na2SO4), and the solvent is evaporated to give N-[4-methoxybenzenesulfonyl]-(D)-leucine, which is used without further purification.

Workup

  1. washwashed successively with 2.5N hydrochloric acid, water, and brine
  2. dry with materialThe organic phase is dried (Na2SO4)
  3. customthe solvent is evaporated

Sources & evidence

ORD record
ord-119ce36be33f4a5b84d887a81121e428
Source dataset
uspto-grants-1996_04
Patent number
US05506242

Linked notes

Loading…