Water → HCID 66672660、化合物

HRID 604549ノート

反応式

HRID 604549 の反応式
[CH3:1][C@@:2]1([CH2:8][CH2:9][C:10]2[N:11]([CH3:15])[CH:12]=[CH:13][CH:14]=2)[CH2:6][O:5][C:4](=[O:7])[NH:3]1.[OH-].[K+].O.[C:19](O)(=O)[C@H:20]([C@@H](C(O)=O)O)[OH:21].O1CCC[CH2:30]1>CO.C(Cl)Cl>[C:4]([O:5][CH2:6][C@@:2]([NH:3][C:20](=[O:21])[CH3:19])([CH3:1])[CH2:8][CH2:9][C:10]1[N:11]([CH3:15])[CH:12]=[CH:13][CH:14]=1)(=[O:7])[CH3:30]

参加物

8

反応物 5

HCID 962WaterHCID 8028TetrahydrofuranHCID 14797Potassium HydroxideHCID 439655D-Tartaric acidHCID 18448138(4R)-4-Methyl-4-[2-(1-methyl-1H-pyrrol-2-yl)ethyl]-1,3-oxazolidin-2-one

生成物 1

HCID 66672660HCID 66672660、化合物収率 53%

試薬・触媒・溶媒 2

HCID 887Methanol溶媒HCID 6344Dichloromethane溶媒

実験手順

(4R)-4-Methyl-4-[2-(1-methylpyrrol-2-yl)ethyl]-1,3-oxazolidin-2-one (17.9 g, 86.0 mmol) obtained in Reference example 1 (1f) was dissolved in a mixture of tetrahydrofuran (250 mL) and methanol (125 mL) and a 5N aqueous potassium hydroxide solution (125 mL) was added thereto, followed by heating under reflux of the mixture for 4 days. After cooling, water and methylene chloride were added to the reaction mixture to separate it. The thus obtained organic phase was separated and dried over anhydrous sodium sulfate. After filtration, the solvent was evaporated under reduced-pressure and the residue was dissolved in ethanol (260 mL). D-(−)-tartaric acid (6.45 g, 43.0 mmol) was added thereto and the mixture was stirred for 2 hours. The precipitated crystal was collected by filtration to obtain a crude crystal (20.7 g). The crude crystal (18.7 g) was recrystallized from a mixture of ethanol (370 mL) and water (37 mL) and the thus obtained crystal was recrystallized again from a mixture of ethanol (300 mL) and water (30 mL). Further, the obtained crystal was recrystallized again from a mixture of ethanol (240 mL) and water (24 mL) to obtain the title compound (10.5 g, yield: 53%) as a colourless scaly crystal.

後処理

  1. temperatureby heating
  2. temperatureunder reflux of the mixture for 4 days
  3. temperatureAfter cooling
  4. customto separate it
  5. customThe thus obtained organic phase was separated
  6. dry with materialdried over anhydrous sodium sulfate
  7. filtrationAfter filtration
  8. customthe solvent was evaporated under reduced-pressure
  9. dissolutionthe residue was dissolved in ethanol (260 mL)
  10. filtrationThe precipitated crystal was collected by filtration
  11. customto obtain a crude crystal (20.7 g)
  12. customThe crude crystal (18.7 g) was recrystallized from a mixture of ethanol (370 mL) and water (37 mL)
  13. customthe thus obtained crystal was recrystallized again from a mixture of ethanol (300 mL) and water (30 mL)
  14. customFurther, the obtained crystal was recrystallized again from a mixture of ethanol (240 mL) and water (24 mL)

出典と根拠

ORDレコード
ord-ed189f5d9e314c4f8f8b35a0c7457911
出典データセット
uspto-grants-2011_03
特許番号
US07910617B2

反応ノート

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