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

HRID 264278

Reaktionsgleichung

Reaktionsgleichung von HRID 264278
[NH2:1][C@@H:2]([C:6]([OH:8])=[O:7])[CH:3]([CH3:5])[CH3:4].O1CCOCC1.O.C(N(CC)CC)C.[CH3:23][O:24][C:25]1[CH:30]=[CH:29][C:28]([S:31](Cl)(=[O:33])=[O:32])=[CH:27][CH:26]=1>C(Cl)Cl>[CH3:23][O:24][C:25]1[CH:26]=[CH:27][C:28]([S:31]([NH:1][C@@H:2]([C:6]([OH:8])=[O:7])[CH:3]([CH3:5])[CH3:4])(=[O:33])=[O:32])=[CH:29][CH:30]=1

Komponenten

6

Edukt 4

HCID 74014-Methoxybenzenesulfonyl chlorideHCID 8471TriethylamineHCID 71563D-ValineHCID 218864351,4-Dioxane--water (1/1)

Produkt 1

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

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To a solution of D-valine (15.0 g, 128.0 mmol) in 1:1 dioxane/water (200 mL) containing triethylamine (19.4 g, 192.0 mmol) at room temperature is added 4-methoxybenzene-sulfonyl chloride (29.0 g, 141.0 mmol), and the reaction mixture is stirred at room temperature overnight. The mixture is then diluted with methylene chloride, washed with 1N aqueous hydrochloric acid and water. The organic layer is washed again with brine, dried (Na2SO4), and the solvent is evaporated to provide N-[4-methoxybenzenesulfonyl]-(D)-valine as a crude product. A solution of this crude product (15.0 g) in toluene (100 mL) containing N,N-dimethylformamide di-t-butyl acetal (50 mL, 206.5 mmol) is heated to 95° C. for 3 hours. The solvent is then evaporated. The crude product is purified by silica gel chromatography (30% ethyl acetate/hexanes) to provide N-[4-methoxybenzene-sulfonyl]-(D)-valine t-butyl ester.

Aufarbeitung

  1. washwashed with 1N aqueous hydrochloric acid and water
  2. washThe organic layer is washed again with brine
  3. dry with materialdried (Na2SO4)
  4. customthe solvent is evaporated

Quellen und Nachweise

ORD-Eintrag
ord-94c9da312d5f43789f00688d9c9edd22
Quelldatensatz
uspto-grants-1997_07
Patentnummer
US05646167

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