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

HRID 265882Notes

Reaction equation

HRID 265882 reaction equation
[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

Participants

6

Reactant 4

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

Product 1

HCID 10754635N-Phenysulfonyl-L-asparagine

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Conditions

Temperature
0 °C

Procedure

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).

Workup

  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

Sources & evidence

ORD record
ord-93f2eb6c74af4b30a4ee0e687ba804a0
Source dataset
uspto-grants-1997_07
Patent number
US05648368

Reaction notes

Loading…