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

HRID 1720580

Reaktionsgleichung

Reaktionsgleichung von HRID 1720580
[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

Komponenten

7

Edukt 3

HCID 74014-Methoxybenzenesulfonyl chlorideHCID 8471TriethylamineHCID 439524D-Leucine

Produkt 1

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

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 962WaterLösungsmittelHCID 6344DichloromethaneLösungsmittelHCID 312751,4-DioxaneLösungsmittel

Versuchsvorschrift

(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.

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-119ce36be33f4a5b84d887a81121e428
Quelldatensatz
uspto-grants-1996_04
Patentnummer
US05506242

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