Hydrazine → HCID 58458554, Verbindung

HRID 44221Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 44221
[C:1]([O:5][C:6]([NH:8][C:9]1([C:13]2[CH:22]=[CH:21][C:16]([C:17](OC)=[O:18])=[CH:15][CH:14]=2)[CH2:12][CH2:11][CH2:10]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[NH2:23][NH2:24]>C(O)C>[NH:23]([C:17]([C:16]1[CH:21]=[CH:22][C:13]([C:9]2([NH:8][C:6](=[O:7])[O:5][C:1]([CH3:4])([CH3:3])[CH3:2])[CH2:12][CH2:11][CH2:10]2)=[CH:14][CH:15]=1)=[O:18])[NH2:24]

Komponenten

4

Edukt 2

HCID 9321HydrazineHCID 58458628HCID 58458628, Verbindung

Produkt 1

HCID 58458554HCID 58458554, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

To a solution of methyl 4-(1-((tert-butoxycarbonyl)amino)cyclobutyl)benzoate (14.8 g, 48 mmol) in ethanol (100 mL) was added hydrazine (12 mL). The reaction mixture was stirred at reflux for 48 hours. The mixture was concentrated in vacuo and the residue was suspended ether (100 mL) and hexanes (50 mL). The suspension was stirred at room temperature for 2 hours and the solid was filtered off and dried under vacuum. The tert-butyl (1-(4-(hydrazinecarbonyl)phenyl)cyclobutyl)carbamate was obtained as a white solid (13.2 g, 89%). M.p.=146-147° C.; 400 MHz 1H NMR (DMSO-d6) δ: 9.70 (s, 1H), 7.75 (d, J=7.6 Hz, 2H), 7.67 (br.s, 1H), 7.42 (d, J=8.4 Hz, 2H), 4.51 (br.s, 2H), 2.37 (br.s, 4H), 2.1-1.9 (m, 1H), 1.85-1.7 (m, 1H), 1.33 (br.s, 9H); LCMS [M+H]: 306.

Aufarbeitung

  1. temperatureat reflux for 48 hours
  2. concentrationThe mixture was concentrated in vacuo
  3. stirringThe suspension was stirred at room temperature for 2 hours
  4. filtrationthe solid was filtered off
  5. customdried under vacuum

Quellen und Nachweise

ORD-Eintrag
ord-4c08f519ad11478a8ed3690598f384ca
Quelldatensatz
uspto-grants-2013_09
Patentnummer
US08541407B2

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