Triethylamine → 4-Oxo-4-[3-(2-oxo-1-pyrrolidinyl)propylamino]butyric acid methyl ester

HRID 892613Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 892613
[NH2:1][CH2:2][CH2:3][CH2:4][N:5]1[CH2:9][CH2:8][CH2:7][C:6]1=[O:10].C(N(CC)CC)C.[C:18]([CH2:22][CH2:23][C:24](Cl)=[O:25])([O:20][CH3:21])=[O:19]>C(Cl)Cl>[CH3:21][O:20][C:18](=[O:19])[CH2:22][CH2:23][C:24](=[O:25])[NH:1][CH2:2][CH2:3][CH2:4][N:5]1[CH2:9][CH2:8][CH2:7][C:6]1=[O:10]

Komponenten

5

Edukt 3

HCID 8471TriethylamineHCID 73888Butanoic acid, 4-chloro-4-oxo-, methyl esterHCID 821111-(3-Aminopropyl)-2-pyrrolidinone

Produkt 1

HCID 539702434-Oxo-4-[3-(2-oxo-1-pyrrolidinyl)propylamino]butyric acid methyl esterAusbeute 88,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To a solution of 1-(3-aminopropyl)-2-oxopyrrolidine (570 mg) in methylene chloride (10 ml) were added triethylamine (0.67 ml) and 3-carbomethoxy propionylchloride (600 mg) in sequence under ice-cooling and the mixture was stirred for 0.5 hour. After 3.5 hours' stirring at room temperature, the reaction mixture was poured into ice water and extracted with chloroform. The organic layer was washed with 1N hydrochloric acid, a saturated aqueous solution of sodium bicarbonate and saturated brine in sequence, and dried over magnesium sulfate, followed by concentration. The residue was purified by silica gel column chromatography (chloroform-methanol) to give 902 mg of 4-oxo-4-[3-(2-oxo-1-pyrrolidinyl)propylamino]butyric acid methyl ester.

Aufarbeitung

  1. temperaturecooling
  2. stirringAfter 3.5 hours' stirring at room temperature
  3. extractionextracted with chloroform
  4. washThe organic layer was washed with 1N hydrochloric acid
  5. dry with materiala saturated aqueous solution of sodium bicarbonate and saturated brine in sequence, and dried over magnesium sulfate
  6. concentrationfollowed by concentration
  7. customThe residue was purified by silica gel column chromatography (chloroform-methanol)

Quellen und Nachweise

ORD-Eintrag
ord-5817a10d96c4487e991cfff161e5aa83
Quelldatensatz
uspto-grants-1992_06
Patentnummer
US05118811

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