Water → tert-butyl (6R,7R)-7-(4-chloro-3-fluorophenyl)-6-{[3-(hydrazinocarbonyl)-2-oxopyridin-1(2H)-yl]methyl}-1,4-oxazepane-4-carboxylate

HRID 1022822Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1022822
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C@@H:8]2[O:14][CH2:13][CH2:12][N:11]([C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])[CH2:10][C@H:9]2[CH2:22][N:23]2[CH:28]=[CH:27][CH:26]=[C:25]([C:29]([O:31]C)=O)[C:24]2=[O:33])=[CH:4][C:3]=1[F:34].O.[NH2:36][NH2:37].O>C(O)C>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C@@H:8]2[O:14][CH2:13][CH2:12][N:11]([C:15]([O:17][C:18]([CH3:19])([CH3:21])[CH3:20])=[O:16])[CH2:10][C@H:9]2[CH2:22][N:23]2[CH:28]=[CH:27][CH:26]=[C:25]([C:29]([NH:36][NH2:37])=[O:31])[C:24]2=[O:33])=[CH:4][C:3]=1[F:34]

Komponenten

5

Edukt 3

HCID 962WaterHCID 24654Hydrazine hydrate (1:1)HCID 66975246HCID 66975246, Verbindung

Produkt 1

HCID 66975927tert-butyl (6R,7R)-7-(4-chloro-3-fluorophenyl)-6-{[3-(hydrazinocarbonyl)-2-oxopyridin-1(2H)-yl]methyl}-1,4-oxazepane-4-carboxylateAusbeute 88,6 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

To a solution of tert-butyl (6R,7R)-7-(4-chloro-3-fluorophenyl)-6-{[3-(methoxycarbonyl)-2-oxopyridin-1(2H)-yl]methyl}-1,4-oxazepane-4-carboxylate (155.7 mg) in ethanol (1.5 mL) was added hydrazine monohydrate (79 mg) at room temperature, and the mixture was heated under reflux for 2 days. The reaction mixture was allowed to cool to room temperature, and poured into water, and the mixture was partitioned with ethyl acetate. The organic layer was washed with brine, and dried over magnesium sulfate. The solvent was evaporated under reduced pressure to give the title compound (138 mg).

Aufarbeitung

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 2 days
  3. customthe mixture was partitioned with ethyl acetate
  4. washThe organic layer was washed with brine
  5. dry with materialdried over magnesium sulfate
  6. customThe solvent was evaporated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-4b6a8bce2172424ba360ee1fe3c7423f
Quelldatensatz
uspto-grants-2014_05
Patentnummer
US08722662B2

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