Water → HCID 10523921, compound

HRID 1964179Notes

Reaction equation

HRID 1964179 reaction equation
[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

Participants

6

Reactant 4

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

Product 1

HCID 10523921HCID 10523921, compoundYield 94%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

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%).

Workup

  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)

Sources & evidence

ORD record
ord-090f184e13dc4f2d809faceeae8e1ebb
Source dataset
uspto-grants-2013_04
Patent number
US08415487B2

Reaction notes

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