Sodium Hydroxide → 4-Pyridylcarbamoyl-beta-alanine

HRID 358556Notes

Reaction equation

HRID 358556 reaction equation
C([O:3][C:4](=[O:17])[CH2:5][CH2:6][NH:7][C:8](=[O:16])[NH:9][C:10]1[CH:15]=[CH:14][N:13]=[CH:12][CH:11]=1)C.[OH-].[Na+]>CO.O>[N:13]1[CH:14]=[CH:15][C:10]([NH:9][C:8]([NH:7][CH2:6][CH2:5][C:4]([OH:17])=[O:3])=[O:16])=[CH:11][CH:12]=1

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 200664534-Pyridylcarbamoyl-beta-alanine ethyl ester

Product 1

HCID 200664464-Pyridylcarbamoyl-beta-alanineYield 95%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

A solution of 2 g (8.4 mmol) of 4-pyridylcarbamoyl-beta-alanine ethyl ester and 0.37 g (9.2 mmol) of sodium hydroxide in 50 ml of methanol and 0.1 ml of water is kept agitated for 24 hr at room temperature. After concentration to dryness, the resulting oily residue is taken up in 15 ml of water. After washing with 3 x 10 ml of dichloromethane, the aqueous phase is acidified with a 3 N hydrochloric acid solution until a pH close to 3 is obtained. The precipitate formed is filtered, washed with 10 ml of cold water and then dried 1.36 g (yield 95%) of 4-pyridylcarbamoyl-beta-alanine is obtained in the form of a solid having a melting point of 222° C.

Workup

  1. concentrationAfter concentration to dryness
  2. washAfter washing with 3 x 10 ml of dichloromethane
  3. customa pH close to 3
  4. customis obtained
  5. customThe precipitate formed
  6. filtrationis filtered
  7. washwashed with 10 ml of cold water

Sources & evidence

ORD record
ord-36809863936945b4b1bcdb47ddd8771b
Source dataset
uspto-grants-1991_03
Patent number
US04997667

Reaction notes

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