4-Methoxybenzenesulfonyl chloride → N-[4-methoxybenzenesulfonyl]-(D)-valine

HRID 742063Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 742063
[NH2:1][C@@H:2]([C:6]([OH:8])=[O:7])[CH:3]([CH3:5])[CH3:4].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>O.CC(C)=O>[CH3:16][O:17][C:18]1[CH:19]=[CH:20][C:21]([S:24]([NH:1][C@@H:2]([C:6]([OH:8])=[O:7])[CH:3]([CH3:5])[CH3:4])(=[O:26])=[O:25])=[CH:22][CH:23]=1

Komponenten

6

Edukt 3

HCID 74014-Methoxybenzenesulfonyl chlorideHCID 8471TriethylamineHCID 71563D-Valine

Produkt 1

HCID 1133588N-[4-methoxybenzenesulfonyl]-(D)-valine

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 180AcetoneLösungsmittel2×HCID 962WaterLösungsmittel

Versuchsvorschrift

To a solution of D-valine (2000 g, 17.09 mol) in water (16.9 L) and acetone (9.5 L), cooled to 5° C., is added triethylamine (4769 mL, 34.22 mol), and the reaction is stirred for 30 minutes. Then a solution of 4-methoxybenzenesulfonyl chloride (3524 g, 18.48 mol) in acetone (7.4 L) is added over 30 minutes, and the reaction is stirred at room temperature overnight. Most of the acetone is evaporated off, and the pH is adjusted to pH=8.25 with 6N sodium hydroxide. The crude product is washed with toluene (2×10 L), and then the pH is re-adjusted to pH=2.2 with 6N hydrochloric acid. The mixture is then extracted with methylene chloride (3×12 L), the combined organic layers are washed with 2N hydrochloric acid, water, dried (Na2SO4), and the solvent is evaporated to provide N-[4-methoxybenzenesulfonyl]-(D)-valine.

Aufarbeitung

  1. stirringthe reaction is stirred at room temperature overnight
  2. customMost of the acetone is evaporated off
  3. washThe crude product is washed with toluene (2×10 L)
  4. extractionThe mixture is then extracted with methylene chloride (3×12 L)
  5. washthe combined organic layers are washed with 2N hydrochloric acid, water
  6. dry with materialdried (Na2SO4)
  7. customthe solvent is evaporated

Quellen und Nachweise

ORD-Eintrag
ord-0b33e831349a4430adec03d09efccd05
Quelldatensatz
uspto-grants-1996_09
Patentnummer
US05552419

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