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Hydrogen chloride-ethyl acetate → (R)-5-(3,4,5-trifluorophenyl)-3,4-dihydro-2H-pyrrole-2-carboxylic acid ethyl ester

HRID 16381
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 16381
[CH2:1]([O:3][C:4](=[O:27])[C@H:5]([NH:19]C(OC(C)(C)C)=O)[CH2:6][CH2:7][C:8](=O)[C:9]1[CH:14]=[C:13]([F:15])[C:12]([F:16])=[C:11]([F:17])[CH:10]=1)[CH3:2].Cl.C(OCC)(=O)C>C(OCC)(=O)C>[CH2:1]([O:3][C:4]([C@H:5]1[CH2:6][CH2:7][C:8]([C:9]2[CH:14]=[C:13]([F:15])[C:12]([F:16])=[C:11]([F:17])[CH:10]=2)=[N:19]1)=[O:27])[CH3:2]
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

4

Edukt 2

HCID 21866389Hydrogen chloride-ethyl acetateHCID 67372607ethyl(R)-2-tert-butoxycarbonylamino-5-oxo-5-(3,4,5-trifluorophenyl)pentanoate

Produkt 1

HCID 67372567(R)-5-(3,4,5-trifluorophenyl)-3,4-dihydro-2H-pyrrole-2-carboxylic acid ethyl esterAusbeute 80,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

To a solution of (R)-2-t-butoxycarbonylamino-5-oxo-5-(3,4,5-trifluorophenyl)valeric acid ethyl ester (22.2 g) in ethyl acetate (30 mL) was added 4 N hydrochloric acid/ethyl acetate (163 mL), and the resultant solution was stirred at room temperature for 3 hours. Solvent was removed by distillation under reduced pressure, and the resulting residue was diluted with ethyl acetate and sodium bicarbonate water. The organic layer was partitioned, washed with brine, and then dried over anhydrous magnesium sulfate. Solvent was removed by distillation under reduced pressure, to thereby obtain the titled compound (12.4 g). The physical properties of this crude product were as follows.

Aufarbeitung

  1. customSolvent was removed by distillation under reduced pressure
  2. additionthe resulting residue was diluted with ethyl acetate and sodium bicarbonate water
  3. customThe organic layer was partitioned
  4. washwashed with brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. customSolvent was removed by distillation under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-295b411d2e014bcf9b491514f041b68b
Quelldatensatz
uspto-grants-2010_06
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07737141B2

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