(-)-Asparagine → N-Phenysulfonyl-L-asparagine

HRID 1532636

Reaktionsgleichung

Reaktionsgleichung von HRID 1532636
[NH2:1][C@H:2]([C:7]([OH:9])=[O:8])[CH2:3][C:4](=[O:6])[NH2:5].[OH-].[Na+].O1CCOCC1.O.[C:19]1([S:25](Cl)(=[O:27])=[O:26])[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1>O>[C:19]1([S:25]([NH:1][C@H:2]([C:7]([OH:9])=[O:8])[CH2:3][C:4](=[O:6])[NH2:5])(=[O:27])=[O:26])[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1

Komponenten

6

Edukt 4

HCID 6267(-)-AsparagineHCID 7369Benzenesulfonyl chlorideHCID 14798Sodium Hydroxide2×HCID 218864351,4-Dioxane--water (1/1)

Produkt 1

HCID 10754635N-Phenysulfonyl-L-asparagine

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Versuchsvorschrift

To L-Asparagine (10 g), add sodium hydroxide (3.4 g) and dioxane/water (50 mL/50 mL). Cool resulting solution in an ice bath and add benzenesulfonyl chloride (10.6 mL), sodium hydroxide (3.4 g), and water (80 mL). Stir for 3 hours. Add water (200 mL) and extract with EtOAc. Acidify the aqueous solution to pH 3 with concentrated HCl and cool to give a precipitate. After 1 hour collect the solid and dry it in vacuo at 40° C. to give the title compound.

Aufarbeitung

  1. temperatureCool
  2. customresulting solution in an ice bath
  3. extractionAdd water (200 mL) and extract with EtOAc
  4. temperaturecool
  5. customto give a precipitate
  6. customAfter 1 hour collect the solid
  7. customdry it in vacuo at 40° C.

Quellen und Nachweise

ORD-Eintrag
ord-afbdb89e85ab49899ea1c627af485223
Quelldatensatz
uspto-grants-2001_03
Patentnummer
US06204282B1

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