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

HRID 265882Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 265882
[NH2:1][C@H:2]([C:7]([OH:9])=[O:8])[CH2:3][C:4](=[O:6])[NH2:5].[OH-].[Na+].O1CCOCC1.[C:18]1([S:24](Cl)(=[O:26])=[O:25])[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1>O>[C:18]1([S:24]([NH:1][C@H:2]([C:7]([OH:9])=[O:8])[CH2:3][C:4](=[O:6])[NH2:5])(=[O:26])=[O:25])[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1

Komponenten

6

Edukt 4

HCID 6267(-)-AsparagineHCID 7369Benzenesulfonyl chlorideHCID 14798Sodium Hydroxide2×HCID 312751,4-Dioxane

Produkt 1

HCID 10754635N-Phenysulfonyl-L-asparagine

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel2×

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

To a stirred solution of L-asparagine (Aldrich) (10 g, 76 mmol), NaOH (3.4 g, 85 mmol), H2O (50 mL), and dioxane (50 mL) at 0° C. was added PhSO2Cl (10.6 mL, 84 mmol). After I min, NaOH (3.4 g) in H2O (50 mL) was added and the reaction mixture stirred for 30 min. The reaction mixture was then concentrated to remove the dioxane then washed with EtOAc. The aqueous phase was then cooled to 0° C. and acidified to pH with cone. HCl to effect product precipitation. The resulting solid was collected by filtration, washed with H2O (20 mL) and dried at 50° C. under vacuum to give 19-1 as a white solid. Rf 0.40 (silica, 10:1:1 ethanol/H2O/NH4OH).

Aufarbeitung

  1. concentrationThe reaction mixture was then concentrated
  2. customto remove the dioxane
  3. washthen washed with EtOAc
  4. customproduct precipitation
  5. filtrationThe resulting solid was collected by filtration
  6. washwashed with H2O (20 mL)
  7. customdried at 50° C. under vacuum

Quellen und Nachweise

ORD-Eintrag
ord-93f2eb6c74af4b30a4ee0e687ba804a0
Quelldatensatz
uspto-grants-1997_07
Patentnummer
US05648368

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