Hydrochloric Acid → Tosyl-L-asparagine

HRID 1458958Notes

Reaction equation

HRID 1458958 reaction equation
[NH2:1][C@H:2]([C:7]([OH:9])=[O:8])[CH2:3][C:4](=[O:6])[NH2:5].[OH-].[Na+].[C:12]1([CH3:22])[CH:17]=[CH:16][C:15]([S:18](Cl)(=[O:20])=[O:19])=[CH:14][CH:13]=1.Cl>O1CCOCC1>[C:12]1([CH3:22])[CH:17]=[CH:16][C:15]([S:18]([NH:1][C@H:2]([C:7]([OH:9])=[O:8])[CH2:3][C:4](=[O:6])[NH2:5])(=[O:20])=[O:19])=[CH:14][CH:13]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 6267(-)-AsparagineHCID 73974-Toluenesulfonyl chlorideHCID 14798Sodium Hydroxide

Product 1

HCID 6995570Tosyl-L-asparagine

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent2×

Procedure

L-Asparagine (10.0 g, 75.7 mmol) was placed in a 500 mL round bottom flask equipped with a magnetic stir bar and an addition funnel. 1N Sodium hydroxide (170 mL, 166.5 mmol) was added along with 50 mL dioxane. p-Toluenesulfonyl chloride (15.88 g, 83.27 mmol) dissolved in dioxane (50 mL) was added to the reaction mixture with vigorous stirring. The reaction mixture was then stirred for 2 h at room temperature, cooled to 0° C., and acidified to pH 2-3 with hydrochloric acid (conc.). The desired product 14-2 formed as a white crystalline solid (20.3 g, 94%) that was collected by filtration.

Workup

  1. customequipped with a magnetic stir bar and an addition funnel
  2. additionwas added to the reaction mixture with vigorous stirring
  3. temperaturecooled to 0° C.

Sources & evidence

ORD record
ord-089705c46b714b13ba02b6857c570aaf
Source dataset
uspto-grants-1998_12
Patent number
US05852045

Reaction notes

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