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

HRID 1871799노트

반응식

HRID 1871799 반응식
[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

참가 물질

6

반응물 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

생성물 1

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

시약·촉매·용매 1

HCID 19096565Water ethanol용매

실험 절차

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

후처리

  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

출처 및 근거

ORD 기록
ord-484c4dcbf2e44d5d8c460c8bf4fe0a9f
출처 데이터셋
uspto-grants-2000_08
특허 번호
USRE036831

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