Methylhydrazine → tert-butyl (6R,7R)-7-(3,4-dichlorophenyl)-6-{[4-(ethoxycarbonyl)-1-methyl-1H-pyrazol-3-yl]methyl}-1,4-oxazepane-4-carboxylate

HRID 1022706Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1022706
CO[CH:3](OC)[N:4]([CH3:6])C.[Cl:9][C:10]1[CH:11]=[C:12]([C@@H:17]2[O:23][CH2:22][CH2:21][N:20]([C:24]([O:26][C:27]([CH3:30])([CH3:29])[CH3:28])=[O:25])[CH2:19][C@H:18]2[CH2:31][C:32](=O)[CH2:33][C:34]([O:36][CH2:37][CH3:38])=[O:35])[CH:13]=[CH:14][C:15]=1[Cl:16].C[NH:41]N>C1(C)C=CC=CC=1>[Cl:9][C:10]1[CH:11]=[C:12]([C@@H:17]2[O:23][CH2:22][CH2:21][N:20]([C:24]([O:26][C:27]([CH3:28])([CH3:30])[CH3:29])=[O:25])[CH2:19][C@H:18]2[CH2:31][C:32]2[C:33]([C:34]([O:36][CH2:37][CH3:38])=[O:35])=[CH:3][N:4]([CH3:6])[N:41]=2)[CH:13]=[CH:14][C:15]=1[Cl:16]

Komponenten

5

Edukt 3

HCID 6061MethylhydrazineHCID 78373Dimethylformamide dimethyl acetalHCID 66976292tert-butyl (6R,7R)-7-(3,4-dichlorophenyl)-6-(4-ethoxy-2,4-dioxobutyl)-1,4-oxazepane-4-carboxylate

Produkt 1

HCID 66975696tert-butyl (6R,7R)-7-(3,4-dichlorophenyl)-6-{[4-(ethoxycarbonyl)-1-methyl-1H-pyrazol-3-yl]methyl}-1,4-oxazepane-4-carboxylateAusbeute 32,5 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1140TolueneLösungsmittel

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

N,N-Dimethylformamide dimethyl acetal (0.210 mL, 1.58 mmol) was added to a solution of tert-butyl (6R,7R)-7-(3,4-dichlorophenyl)-6-(4-ethoxy-2,4-dioxobutyl)-1,4-oxazepane-4-carboxylate (500 mg, 1.05 mmol) in toluene (5 mL), and the mixture was stirred at 80° C. for 2 hr, and concentrated under reduced pressure. The residue was dissolved in ethanol (5 mL), and methylhydrazine (0.062 mL, 1.16 mmol) was added. The reaction mixture was stirred at 80° C. for 1.5 hr, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography to give the title compound (175 mg).

Aufarbeitung

  1. concentrationconcentrated under reduced pressure
  2. dissolutionThe residue was dissolved in ethanol (5 mL)
  3. stirringThe reaction mixture was stirred at 80° C. for 1.5 hr
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by silica gel column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-537fc123c3e64b159cf595a97744cb07
Quelldatensatz
uspto-grants-2014_05
Patentnummer
US08722662B2

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