Beta-Alanine → N-(methylsulfonyl)-beta-alanine

HRID 2309824Notes

Reaction equation

HRID 2309824 reaction equation
[NH2:1][CH2:2][CH2:3][C:4]([OH:6])=[O:5].[CH3:7][S:8](Cl)(=[O:10])=[O:9].[OH-].[Na+]>CO>[CH3:7][S:8]([NH:1][CH2:2][CH2:3][C:4]([OH:6])=[O:5])(=[O:10])=[O:9]

Participants

5

Reactant 3

HCID 239Beta-AlanineHCID 14798Sodium HydroxideHCID 31297Methanesulfonyl chloride

Product 1

HCID 6502032N-(methylsulfonyl)-beta-alanine

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

22.3 g of β-alanine are dissolved in 125 ml of 2N MeOH. 20 ml of methanesulfonyl chloride and 145 ml of 2N NaOH are simultaneously added dropwise at 0°-5° C., with vibromixing, and the mixture is vibrated at room temperature for 3 hours. The solution is extracted with ether and the extract is diluted to 400 ml and stirred with a strongly acid ion exchanger (Lewatit® S 100) until the pH reaches about 2. The solution is then evaporated to dryness in vacuo. The residue is taken up in ethyl acetate, the mixture is dried over sodium sulfate and DCA is added until an alkaline reaction is obtained. The precipitate which separates out is filtered off, washed with ethyl acetate and ether, dried and recrystallized from tetrahydrofuran.

Workup

  1. extractionThe solution is extracted with ether
  2. additionthe extract is diluted to 400 ml
  3. customThe solution is then evaporated to dryness in vacuo
  4. dry with materialthe mixture is dried over sodium sulfate and DCA
  5. additionis added until an alkaline reaction
  6. customis obtained
  7. filtrationThe precipitate which separates out is filtered off
  8. washwashed with ethyl acetate and ether
  9. customdried
  10. customrecrystallized from tetrahydrofuran

Sources & evidence

ORD record
ord-4a9dd2c0d4494481871df9ad08727f65
Source dataset
uspto-grants-1987_09
Patent number
US04696913

Reaction notes

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