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

HRID 1532636

Reaction equation

HRID 1532636 reaction equation
[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

Participants

6

Reactant 4

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

Product 1

HCID 10754635N-Phenysulfonyl-L-asparagine

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

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.

Workup

  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.

Sources & evidence

ORD record
ord-afbdb89e85ab49899ea1c627af485223
Source dataset
uspto-grants-2001_03
Patent number
US06204282B1

Linked notes

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