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

HRID 583649Notes

Reaction equation

HRID 583649 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 1 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 dioxane then washed with EtOAc. The aqueous phase was then cooled to 0° C. and acidified to pH 5.0 with conc. 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 N-phenylsulfonyl-L-asparagine (2-1a) as a white solid.

Workup

  1. concentrationThe reaction mixture was then concentrated
  2. customto remove 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-3edb8ad749e44a618e65b76d14d1e246
Source dataset
uspto-grants-1999_07
Patent number
US05929120

Reaction notes

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