Tert-butyl 4-cyanophenylcarbamate → HCID 178507458, Verbindung

HRID 2103936

Reaktionsgleichung

Reaktionsgleichung von HRID 2103936
C(OC([NH:8][C:9]1[CH:16]=[CH:15][C:12]([C:13]#[N:14])=[CH:11][CH:10]=1)=O)(C)(C)C.O1CC(=O)N=N1.C(OC(=O)CCNC(=O)C1C=CC(C2[NH:38][O:39][C:40](=[O:42])N=2)=CC=1)C>C(Cl)Cl.C(O)(C(F)(F)F)=O>[O:39]1[C:40](=[O:42])[N:14]=[C:13]([C:12]2[CH:11]=[CH:10][C:9]([NH2:8])=[CH:16][CH:15]=2)[NH:38]1

Komponenten

6

Edukt 3

HCID 10130644Tert-butyl 4-cyanophenylcarbamateHCID 21866502OxadiazoloneHCID 178472065HCID 178472065, Verbindung

Produkt 1

HCID 178507458HCID 178507458, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6344DichloromethaneLösungsmittelHCID 6422Trifluoroacetic acidLösungsmittel

Versuchsvorschrift

Compound 14 (3.25 g, 14.9 mmol) was converted into oxadiazolone 15 as described earlier for the preparation of compound 3. The resulting crude light orange solid was stirred for 5 h in a mixture of DCM (15 mL) and TFA (8 mL). Concentration under reduced pressure and evaporation with toluene (2×10 mL) gave a brown solid which was purified by silica gel (40 g) column chromatography (eluent: EtOAc) to yield compound 16 (1.81 g, 69% over the three steps). Rf 0.5 (EtOAc).

Aufarbeitung

  1. concentrationConcentration
  2. customunder reduced pressure and evaporation with toluene (2×10 mL)
  3. customgave a brown solid which
  4. customwas purified by silica gel (40 g) column chromatography (eluent: EtOAc)

Quellen und Nachweise

ORD-Eintrag
ord-80977cb623b04e04bafd62ef3fce6e2f
Quelldatensatz
uspto-grants-2009_08
Patentnummer
US07576071B2

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