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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 1677076
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1677076
Cl.C(OCC)(=O)C.[CH2:8]([O:10][C:11](=[O:34])[C@H:12]([NH:26]C(OC(C)(C)C)=O)[CH2:13][CH2:14][C:15](=O)[C:16]1[CH:21]=[C:20]([F:22])[C:19]([F:23])=[C:18]([F:24])[CH:17]=1)[CH3:9]>C(OCC)(=O)C>[CH2:8]([O:10][C:11]([C@H:12]1[CH2:13][CH2:14][C:15]([C:16]2[CH:21]=[C:20]([F:22])[C:19]([F:23])=[C:18]([F:24])[CH:17]=2)=[N:26]1)=[O:34])[CH3:9]
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

4 N hydrochloric acid/ethyl acetate (163 mL) was added to an ethyl acetate (30 mL) solution of (R)-2-t-butoxycarbonylamino-5-oxo-5-(3,4,5-trifluorophenyl) valeric acid ethyl ester (22.2 g), and stirring was continued for 3 hours at room temperature. The solvent was removed under a vacuum, and ethyl acetate and sodium bicarbonate aqueous solution were added to the residue, and the organic layer was partitioned. After washing the organic layer with brine, the resultant was dried over anhydrous magnesium sulfate. The solvent was removed under a vacuum, and the title compound (12.4 g) was obtained. The physical property values are as follows.

Aufarbeitung

  1. customThe solvent was removed under a vacuum, and ethyl acetate and sodium bicarbonate aqueous solution
  2. additionwere added to the residue
  3. customthe organic layer was partitioned
  4. washAfter washing the organic layer with brine
  5. dry with materialthe resultant was dried over anhydrous magnesium sulfate
  6. customThe solvent was removed under a vacuum

Quellen und Nachweise

ORD-Eintrag
ord-f864a765db4b42fa9fca7eceaed93418
Quelldatensatz
uspto-grants-2011_08
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08008293B2

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