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

HRID 264336

Reaktionsgleichung

Reaktionsgleichung von HRID 264336
[NH2:1][C@@H:2]([C:6]([OH:8])=[O:7])[C@H:3]([CH3:5])[OH: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.O1CCOCC1>[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])[C@H:3]([CH3:5])[OH:4])(=[O:26])=[O:25])=[CH:22][CH:23]=1

Komponenten

6

Edukt 3

HCID 74014-Methoxybenzenesulfonyl chlorideHCID 8471TriethylamineHCID 69435D-Threonine

Produkt 1

HCID 2104039N-[4-methoxybenzenesulfonyl]-(D)-threonine

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 312751,4-DioxaneLösungsmittel

Versuchsvorschrift

To a solution of D-threonine (5.0 g, 0.042 mol) in water (50 mL) and dioxane (50 mL) containing triethylamine (8.9 mL, 0.063 mol) at room temperature is added 4-methoxybenzenesulfonyl chloride (9.54 g, 0.046 mol). The reaction mixture is stirred overnight at room temperature. Most of the dioxane is evaporated off, and the pH is adjusted to pH=2 with 1N HCl. The mixture is then extracted with ethyl acetate. The combined organic extracts are washed with brine, dried (Na2SO4), and concentrated in vacuo to provide N-[4-methoxybenzenesulfonyl]-(D)-threonine.

Aufarbeitung

  1. customMost of the dioxane is evaporated off
  2. extractionThe mixture is then extracted with ethyl acetate
  3. washThe combined organic extracts are washed with brine
  4. dry with materialdried (Na2SO4)
  5. concentrationconcentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-6c15a3f3f4cf44b0b864b35e03ca18c9
Quelldatensatz
uspto-grants-1997_07
Patentnummer
US05646167

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