Beta-Alanine → 3-(3,4-Dimethoxybenzenesulfonamido)propanoic acid

HRID 133088Notes

Reaction equation

HRID 133088 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([S:11](Cl)(=[O:13])=[O:12])[CH:6]=[CH:7][C:8]=1[O:9][CH3:10].[NH2:15][CH2:16][CH2:17][C:18]([OH:20])=[O:19].C(O)(=O)CC(CC(O)=O)(C(O)=O)O>O1CCOCC1.[OH-].[Na+]>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([S:11]([NH:15][CH2:16][CH2:17][C:18]([OH:20])=[O:19])(=[O:13])=[O:12])[CH:6]=[CH:7][C:8]=1[O:9][CH3:10]

Participants

6

Reactant 3

HCID 239Beta-AlanineHCID 311Citric AcidHCID 27341833,4-Dimethoxybenzenesulfonyl chloride

Product 1

HCID 75737343-(3,4-Dimethoxybenzenesulfonamido)propanoic acid

Reagents, catalysts & solvents 2

HCID 14798Sodium HydroxideSolventHCID 312751,4-DioxaneSolvent

Procedure

A solution of 3.8 g of 3,4-dimethoxybenzenesulfonyl chloride in 5 ml of dioxane is added dropwise to a solution of 1.5 g of 3-aminopropionic acid in 20 ml of 1N NaOH solution. The mixture is left to stir while controlling the pH (pH>7) for 12 h, the pH is reduced below 7 by adding citric acid, and the reaction solution is then extracted with methylene chloride. The organic phase is dried over magnesium sulfate, concentrated under reduced pressure and employed without further purification in the next reaction step. The desired product is obtained with MW=289.31 (calculated); measured value (M+H)+: 290.1

Workup

  1. waitThe mixture is left
  2. customfor 12 h
  3. extractionthe reaction solution is then extracted with methylene chloride
  4. dry with materialThe organic phase is dried over magnesium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customemployed without further purification in the next reaction step

Sources & evidence

ORD record
ord-df3df68e36ce49d099fb036a384909c2
Source dataset
uspto-grants-2008_06
Patent number
US07390814B2

Reaction notes

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