Pyridine → (2S,4EZ)-4-[(allyloxy)imino)-1-(tert-butoxycarbonyl)-2-pyrrolidinecarboxylic acid

HRID 457910

Reaktionsgleichung

Reaktionsgleichung von HRID 457910
[C:1]([O:5][C:6]([N:8]1[CH2:12][C:11](=O)[CH2:10][C@H:9]1[C:14]([OH:16])=[O:15])=[O:7])([CH3:4])([CH3:3])[CH3:2].O.Cl.[CH2:19]([O:22][NH2:23])[CH:20]=[CH2:21].N1C=CC=CC=1>C(O)C>[CH2:19]([O:22][N:23]=[C:11]1[CH2:12][N:8]([C:6]([O:5][C:1]([CH3:4])([CH3:3])[CH3:2])=[O:7])[C@H:9]([C:14]([OH:16])=[O:15])[CH2:10]1)[CH:20]=[CH2:21]

Komponenten

5

Edukt 3

HCID 1049PyridineHCID 11593804(2S)-1-(tert-butoxycarbonyl)-4-oxopyrrolidine-2-carboxylic acidHCID 16211718O-Prop-2-en-1-ylhydroxylamine--hydrogen chloride--water (1/1/1)

Produkt 1

HCID 58714562(2S,4EZ)-4-[(allyloxy)imino)-1-(tert-butoxycarbonyl)-2-pyrrolidinecarboxylic acidAusbeute 94,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

A solution was made containing (2S)-1-(tert-butoxycarbonyl)-4-oxo-2-pyrrolidinecarboxylic acid (5.0 g, 22 mmol) and O-allylhydroxylamine hydrochloride monohydrate (7.2 g, 65.5 mmol) in a 1:1 mixture of pyridine and ethanol (100 ml). The reaction was heated to reflux for 2.5 h before cooling and removal of solvent. The residue was dissolved in ethyl acetate and washed rapidly with 1.3N HCl (40 ml). The acidic layer was then extracted with ethyl acetate (3×20 ml) and the combined organic layers washed with brine before drying over magnesium sulfate, filtering and removal of solvent in vacuo. The desired product (5.9 g, 94%) was isolated as a pale yellow oil.

Aufarbeitung

  1. temperatureThe reaction was heated
  2. temperatureto reflux for 2.5 h
  3. temperaturebefore cooling
  4. customremoval of solvent
  5. dissolutionThe residue was dissolved in ethyl acetate
  6. washwashed rapidly with 1.3N HCl (40 ml)
  7. extractionThe acidic layer was then extracted with ethyl acetate (3×20 ml)
  8. washthe combined organic layers washed with brine
  9. dry with materialbefore drying over magnesium sulfate
  10. filtrationfiltering
  11. customremoval of solvent in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-67cacd03687843d0887584299ec1b0f7
Quelldatensatz
uspto-grants-2007_03
Patentnummer
US07189754B2

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