Trifluoroacetic acid → HCID 63761213, Verbindung

HRID 2421992Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2421992
[Cl:1][C:2]1[C:3]([N:12]2[CH2:15][CH:14]([NH:16]C(=O)OC(C)(C)C)[CH2:13]2)=[N:4][CH:5]=[C:6]([C:8]([F:11])([F:10])[F:9])[CH:7]=1.C(O)(C(F)(F)F)=O>C(Cl)Cl>[Cl:1][C:2]1[C:3]([N:12]2[CH2:13][CH:14]([NH2:16])[CH2:15]2)=[N:4][CH:5]=[C:6]([C:8]([F:10])([F:11])[F:9])[CH:7]=1

Komponenten

4

Edukt 2

HCID 6422Trifluoroacetic acidHCID 86625879HCID 86625879, Verbindung

Produkt 1

HCID 63761213HCID 63761213, VerbindungAusbeute 95,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

tert-Butyl {1-[3-chloro-5-(trifluoromethyl)pyridin-2-yl]azetidin-3-yl}carbamate (0.85 g, 2.42 mmol) was dissolved in DCM (4 mL) and TFA (3 mL) and stirred at rt for 1 h. The mixture was concentrated and redissolved in EtOAc, washed with saturated aqueous K2CO3. The organic layer was dried with Na2SO4, filtered and evaporated affording the title compound (0.58 g, 95.1%). 1H NMR (500 MHz, CDCl3): δ 1.65 (bs, 2H), 3.91-3.98 (m, 3H), 4.57-4.61 (m, 2H), 7.58 (s, 1H), 8.26 (s, 1H); 13C NMR (125 MHz, CDCl3): δ 43.68, 63.02, 115.38, 116.90 (q, JC-F=33.2 Hz), 123.91 (q, JC-F=270.9 Hz), 134.95, 143.76, 157.56; Mass Spectrum: M+H+ 252.

Aufarbeitung

  1. concentrationThe mixture was concentrated
  2. dissolutionredissolved in EtOAc
  3. washwashed with saturated aqueous K2CO3
  4. dry with materialThe organic layer was dried with Na2SO4
  5. filtrationfiltered
  6. customevaporated

Quellen und Nachweise

ORD-Eintrag
ord-503b4b05e126417b99253d57e9583410
Quelldatensatz
uspto-grants-2011_06
Patentnummer
US07960380B2

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