Water → HCID 10523921, 화합물

HRID 557475노트

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HRID 557475 반응식
[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

참가 물질

6

반응물 4

HCID 962WaterHCID 6420Trichloroacetyl chloride3회HCID 516892Sodium BicarbonateHCID 10823690Ethyl (3R)-2,5-dioxo-3-(1H-pyrrol-1-yl)-3-pyrrolidinecarboxylate

생성물 1

HCID 10523921HCID 10523921, 화합물수율 94%

시약·촉매·용매 1

HCID 8857Ethyl Acetate용매

실험 절차

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%).

후처리

  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)

출처 및 근거

ORD 기록
ord-26033c0c8710423c9620ff1b69b9930c
출처 데이터셋
uspto-grants-2011_11
특허 번호
US08058456B2

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