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Benzoic Acid → Tert-butyl 4-(5-phenyl-1,2,4-oxadiazol-3-yl)piperazine-1-carboxylate

HRID 888179
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 888179
[OH:1][NH:2][C:3](=[NH:17])[N:4]1[CH2:9][CH2:8][N:7]([C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11])[CH2:6][CH2:5]1.[C:18](O)(=O)[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1.C(N=C=NC(C)C)(C)C>C(Cl)Cl.N1C=CC=CC=1>[C:19]1([C:18]2[O:1][N:2]=[C:3]([N:4]3[CH2:5][CH2:6][N:7]([C:10]([O:12][C:13]([CH3:14])([CH3:16])[CH3:15])=[O:11])[CH2:8][CH2:9]3)[N:17]=2)[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 3

HCID 243Benzoic AcidHCID 12734DiisopropylcarbodiimideHCID 178452346tert-butyl 4-(N-hydroxyamidino)-piperazine-1-carboxylate

Produkt 1

HCID 11992900Tert-butyl 4-(5-phenyl-1,2,4-oxadiazol-3-yl)piperazine-1-carboxylateAusbeute 53 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 1049PyridineLösungsmittel
HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To a solution of tert-butyl 4-[(hydroxyamino)(imino)methyl]piperazine-1-carboxylate (7 g, 28.6 mmol) in anhydrous DCM (150 mL) was added benzoic acid (3.49 g, 28.6 mmol) followed by diisopropyl carbodiimide (DIC, 3.6 g, 28.6 mmol). The reaction mixture was stirred at RT for 8 hours and filtered. The filtrate was evaporated and the residue obtained was refluxed in pyridine (100 mL) for 3 hours. The solvent was removed under vacuum and the residue was dissolved in DCM. The organic layer was washed with a 10% aqueous solution of sodium bicarbonate, water and brine. The organic layer was dried and the solvent was evaporated. The residue was purified by chromatography using petrol ether/EtOAc (9/1) as eluent to afford 5 g (53%) of the title compound as a solid. TLC-Pet ether/EtOAc (9/1): Rf=0.7). HPLC purity: 96%.

Aufarbeitung

  1. filtrationfiltered
  2. customThe filtrate was evaporated
  3. customthe residue obtained
  4. customThe solvent was removed under vacuum
  5. dissolutionthe residue was dissolved in DCM
  6. washThe organic layer was washed with a 10% aqueous solution of sodium bicarbonate, water and brine
  7. customThe organic layer was dried
  8. customthe solvent was evaporated
  9. customThe residue was purified by chromatography

Quellen und Nachweise

ORD-Eintrag
ord-ab035be599a8471596c50f2c78cb1f59
Quelldatensatz
uspto-grants-2012_08
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08247437B2

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