Beta-Alanine → 3-Benzyloxy-1-(2'-carboxyethyl)-2-methylpyrid-4-one

HRID 1906185Notes

Reaction equation

HRID 1906185 reaction equation
[CH2:1]([O:8][C:9]1[C:14](=[O:15])[CH:13]=[CH:12]O[C:10]=1[CH3:16])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(OC1C(=O)C=COC=1C)C1C=CC=CC=1.C(N1C=CC(=O)C(O)=C1C)(=O)C.[NH2:45][CH2:46][CH2:47][C:48]([OH:50])=[O:49].[OH-].[Na+]>O.C(O)C>[CH2:1]([O:8][C:9]1[C:14](=[O:15])[CH:13]=[CH:12][N:45]([CH2:46][CH2:47][C:48]([OH:50])=[O:49])[C:10]=1[CH3:16])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 239Beta-AlanineHCID 14798Sodium HydroxideHCID 14901193-Benzyloxy-2-methyl-4-pyroneHCID 867413491-acetyl-3-hydroxy-2-methylpyrid-4-one 3-Benzyloxy-2-methyl-4-pyrone

Product 1

HCID 4046793-Benzyloxy-1-(2'-carboxyethyl)-2-methylpyrid-4-oneYield 70%

Reagents, catalysts & solvents 1

HCID 19096565Water ethanolSolvent

Procedure

3-Benzyloxy-2-methyl-4-pyrone, prepared as described under (J), (20 g) and beta-alanine (9 g) are dissolved in 3:2 v/v water/ethanol (500 ml) containing NaOH (10 g) to provide a solution with a pH of at least 13. The solution is refluxed for 15 minutes whereupon it turns from a light orange to an intense red colour. The solution is acidified to pH 7.0 and the ethanol is removed by rotary evaporation. The resulting aqueous solution is washed twice with ethylacetate (100 ml). This solution is then subjected to rotary evaporation until the volume is reduced to 100 ml and this reduced volume of solution is acidified to pH 3.0 to give a white precipitate, which is filtered off to give 3-benzyloxy-1-(2'-carboxyethyl)-2-methylpyrid-4-one in 70% yield, m.p. 156°-157° C. 1-(2'-Carboxyethyl)-3-hydroxy-2-methylpyrid-4-one hydrochloride

Workup

  1. customto provide a solution with a pH of at least 13
  2. temperatureThe solution is refluxed for 15 minutes whereupon it
  3. customthe ethanol is removed by rotary evaporation
  4. washThe resulting aqueous solution is washed twice with ethylacetate (100 ml)
  5. customThis solution is then subjected to rotary evaporation until the volume
  6. customto give a white precipitate, which
  7. filtrationis filtered off

Sources & evidence

ORD record
ord-283196e4511341cd883533b07a945ad6
Source dataset
uspto-grants-1987_03
Patent number
US04650793

Reaction notes

Loading…