Water → HCID 10523921、化合物

HRID 557475ノート

反応式

HRID 557475 の反応式
[O:1]=[C:2]1[C@@:6]([N:12]2[CH:16]=[CH:15][CH:14]=[CH:13]2)([C:7]([O:9][CH2:10][CH3:11])=[O:8])[CH2:5][C:4](=[O:17])[NH:3]1.[Cl:18][C:19]([Cl:24])([Cl:23])[C:20](Cl)=[O:21].O.C(=O)(O)[O-].[Na+]>C(OCC)(=O)C>[O:1]=[C:2]1[C@@:6]([N:12]2[CH:13]=[CH:14][CH:15]=[C:16]2[C:20](=[O:21])[C:19]([Cl:24])([Cl:23])[Cl:18])([C:7]([O:9][CH2:10][CH3:11])=[O:8])[CH2:5][C:4](=[O:17])[NH:3]1

参加物

6

反応物 4

HCID 962WaterHCID 6420Trichloroacetyl chloride3 回HCID 516892Sodium BicarbonateHCID 10823690Ethyl (3R)-2,5-dioxo-3-(1H-pyrrol-1-yl)-3-pyrrolidinecarboxylate

生成物 1

HCID 10523921HCID 10523921、化合物収率 94%

試薬・触媒・溶媒 1

HCID 8857Ethyl Acetate溶媒

実験手順

To a solution of ethyl (R)-2,5-dioxo-3-(pyrrol-1-yl)pyrrolidine-3-carboxylate (767 mg) in ethyl acetate (10 ml) was added trichloroacetyl chloride (1.1 ml) and this solution was heated under reflux overnight. This reaction mixture was allowed to cool to room temperature, and thereto was added trichloroacetyl chloride (1.1 ml) and this mixture was heated under reflux for 3 hours. This reaction mixture was allowed to water-cooling to room temperature and the residual trichloroacetyl chloride was decomposed carefully with saturated aqueous sodium bicarbonate solution. After the aqueous layer was confirmed to be alkali, this mixture was extracted with ethyl acetate (5 ml) three times and the combined extract was washed sequentially with water and saturated brine, dried over magnesium sulfate, filtered and then concentrated to give a crude product as oil. This was purified by a flash column chromatography (n-hexane:ethyl acetate=1:1) to give ethyl (R)-2,5-dioxo-3-(2-trichloroacetylpyrrol-1-yl)pyrrolidine-3-carboxylate (1.17 g, 94%).

後処理

  1. temperaturethis solution was heated
  2. temperatureunder reflux overnight
  3. temperaturethis mixture was heated
  4. temperatureunder reflux for 3 hours
  5. temperaturecooling to room temperature
  6. extractionthis mixture was extracted with ethyl acetate (5 ml) three times
  7. extractionthe combined extract
  8. washwas washed sequentially with water and saturated brine
  9. dry with materialdried over magnesium sulfate
  10. filtrationfiltered
  11. concentrationconcentrated
  12. customto give a crude product as oil
  13. customThis was purified by a flash column chromatography (n-hexane:ethyl acetate=1:1)

出典と根拠

ORDレコード
ord-26033c0c8710423c9620ff1b69b9930c
出典データセット
uspto-grants-2011_11
特許番号
US08058456B2

反応ノート

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