Trifluoroacetic acid → 3,3-Bis(4-chlorophenyl)-1-(2-oxo-2-piperazin-1-ylethyl)pyrrolidin-2-one

HRID 2408855Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2408855
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2([C:30]3[CH:35]=[CH:34][C:33]([Cl:36])=[CH:32][CH:31]=3)[CH2:12][CH2:11][N:10]([CH2:13][C:14]([N:16]3[CH2:21][CH2:20][N:19](C(OC(C)(C)C)=O)[CH2:18][CH2:17]3)=[O:15])[C:9]2=[O:29])=[CH:4][CH:3]=1.FC(F)(F)C(O)=O>C(Cl)Cl>[Cl:36][C:33]1[CH:34]=[CH:35][C:30]([C:8]2([C:5]3[CH:4]=[CH:3][C:2]([Cl:1])=[CH:7][CH:6]=3)[CH2:12][CH2:11][N:10]([CH2:13][C:14](=[O:15])[N:16]3[CH2:21][CH2:20][NH:19][CH2:18][CH2:17]3)[C:9]2=[O:29])=[CH:31][CH:32]=1

Komponenten

4

Edukt 2

HCID 6422Trifluoroacetic acidHCID 86657628tert-Butyl 4-(2-(3,3-bis(4-chlorophenyl)-2-oxopyrrolidin-1-yl)acetyl)piperazine-1-carboxylate

Produkt 1

HCID 533901173,3-Bis(4-chlorophenyl)-1-(2-oxo-2-piperazin-1-ylethyl)pyrrolidin-2-one

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To a solution of the product from Example 25E (0.920 g, 1.73 mmol) in CH2Cl2 (20 mL) was added trifluoroacetic acid (2.66 mL, 34.6 mmol) under nitrogen. The reaction mixture was stirred overnight at room temperature. The reaction mixture was concentrated to remove excess trifluoroacetic acid and then diluted with CH2Cl2 (150 ml). The organic layer was washed with saturated aqueous NaHCO3 solution, water, and brine, dried with MgSO4, filtered, and concentrated. Purification by chromatography on silica gel, eluting with 7N NH3 in CH3OH/CH2Cl2, 3:97) yielded the title compound: 1H NMR (300 MHz, DMSO-d6) δ ppm 7.42-7.30 (m, 8H), 4.16 (s, 2H), 3.40-3.29 (m, 7H), 2.75-2.59 (m, 6H).

Aufarbeitung

  1. concentrationThe reaction mixture was concentrated
  2. customto remove excess trifluoroacetic acid
  3. additiondiluted with CH2Cl2 (150 ml)
  4. washThe organic layer was washed with saturated aqueous NaHCO3 solution, water, and brine
  5. dry with materialdried with MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customPurification by chromatography on silica gel
  9. washeluting with 7N NH3 in CH3OH/CH2Cl2, 3:97)

Quellen und Nachweise

ORD-Eintrag
ord-cede88c441d445569e5410f5d4630832
Quelldatensatz
uspto-grants-2014_08
Patentnummer
US08815869B2

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