Methanol → 2,3-Dihydroxybutanedioic Acid

HRID 1861534ノート

反応式

HRID 1861534 の反応式
[CH:1]1[C:14]2[N:13]([CH2:15][CH2:16][O:17][C:18]3[CH:23]=[CH:22][C:21]([CH2:24][CH:25]([O:31][CH2:32][CH3:33])[C:26]([O:28]CC)=[O:27])=[CH:20][CH:19]=3)[C:12]3[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=3)[O:6][C:5]=2[CH:4]=[CH:3][CH:2]=1.[CH3:34][OH:35].[OH-:36].[Na+].[OH2:38]>>[CH:25]([OH:31])([C:26]([OH:28])=[O:27])[CH:24]([OH:38])[C:34]([OH:36])=[O:35].[CH:1]1[C:14]2[N:13]([CH2:15][CH2:16][O:17][C:18]3[CH:19]=[CH:20][C:21]([CH2:24][CH:25]([O:31][CH2:32][CH3:33])[C:26]([OH:28])=[O:27])=[CH:22][CH:23]=3)[C:12]3[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=3)[O:6][C:5]=2[CH:4]=[CH:3][CH:2]=1

参加物

6

反応物 4

HCID 887MethanolHCID 962WaterHCID 14798Sodium HydroxideHCID 9803656Racemic ethyl 3-[4[2(phenoxazin-10-yl)ethoxy]phenyl]-2-ethoxypropionate3 回

生成物 2

HCID 8752,3-Dihydroxybutanedioic AcidHCID 4630913Ragaglitazar(racemate)

実験手順

To a mixture of racemic ethyl 3-[4-[2-(phenoxazin-10-yl)ethoxy]phenyl]-2-ethoxypropionate of the formula (4) (45 g) obtained according to the procedure described in step (vi) above and methanol (225 ml) was added aqueous 10% sodium hydroxide solution (225 ml) slowly at room temperature over a period of 10-15 minutes. The reaction mixture was stirred at the same temperature for a period of 2-4 h. The progress of the reaction was monitored by TLC. After the complete hydrolysis of the compound of the formula (4), the reaction mass was diluted with water (225 ml) and washed with toluene to remove the impurities. The aqueous layer was acidified with dilute hydrochloric acid and extracted with toluene. Combined organic extracts were washed with water and concentrated under reduced pressure to half the volume and treated with activated charcoal. Filtration of the charcoal followed by concentration of toluene to ˜50 ml and precipitation with pet ether afforded racemic acid of the formula (5) as an off-white to white solid which was filtered and dried at room temperature (˜30° C.), (38-39 g, 90-92%).

後処理

  1. customobtained
  2. washwashed with toluene
  3. customto remove the impurities
  4. extractionextracted with toluene
  5. washCombined organic extracts were washed with water
  6. concentrationconcentrated under reduced pressure to half the volume
  7. additiontreated with activated charcoal
  8. filtrationFiltration of the charcoal
  9. customfollowed by concentration of toluene to ˜50 ml and precipitation with pet ether

出典と根拠

ORDレコード
ord-13e24a2421fb4bde8440573ed7b32381
出典データセット
uspto-grants-2003_03
特許番号
US06531596B1

反応ノート

読み込み中…