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

HRID 979238Notes

Reaction equation

HRID 979238 reaction equation
[NH2:1][CH2:2][CH2:3][C:4]([OH:6])=[O:5].[CH2:7]([O:14][C:15]1[C:20](=[O:21])[CH:19]=[CH:18]O[C:16]=1[CH3:22])[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.[OH-].[Na+].Cl>O.C(O)C>[CH2:7]([O:14][C:15]1[C:20](=[O:21])[CH:19]=[CH:18][N:1]([CH2:2][CH2:3][C:4]([OH:6])=[O:5])[C:16]=1[CH3:22])[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1

Participants

7

Reactant 4

HCID 239Beta-AlanineHCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 14901193-Benzyloxy-2-methyl-4-pyrone

Product 1

HCID 4046793-Benzyloxy-1-(2'-carboxyethyl)-2-methylpyrid-4-one

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent2×

Procedure

β-Alanine (5 g) in water (50 ml) is added to 3-benzyloxy-2-methyl-4-pyrone (10 g) in 95% ethanol (100 ml) and sodium hydroxide (4 g) in water (50 ml) is then slowly added to the reaction mixture until a pH of 13 is obtained. The solution is refluxed for 15 minutes during which time the colour changes from yellow to amber. After cooling, the solution is acidified to pH 2.5 with concentrated HCl (about 2 ml) and is then rotary evaporated at 50° C. The resulting oil is subjected to a methylene chloride/water extraction. The solid which remains is triturated with acetone and recrystallised from water to give 3-benzyloxy-1-(2'-carboxyethyl)-2-methylpyrid-4-one, m.p. 81°-83° C.

Workup

  1. additionis then slowly added to the reaction mixture until a pH of 13
  2. customis obtained
  3. temperatureThe solution is refluxed for 15 minutes during which time the colour changes from yellow
  4. temperatureAfter cooling
  5. customis then rotary evaporated at 50° C
  6. extractionThe resulting oil is subjected to a methylene chloride/water extraction
  7. customThe solid which remains is triturated with acetone
  8. customrecrystallised from water

Sources & evidence

ORD record
ord-fdf85418b6174300991d97c2e910420a
Source dataset
uspto-grants-1987_05
Patent number
US04666927

Reaction notes

Loading…