Sodium Iodide → HCID 66976194, Verbindung

HRID 1022722Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1022722
[H-].[Na+].[Cl:3][C:4]1[CH:5]=[C:6]([CH:11]2[O:17][CH2:16][CH2:15][N:14]([C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])[CH2:13][CH:12]2[OH:25])[CH:7]=[CH:8][C:9]=1[Cl:10].Cl[C:27]1[N:32]=[C:31]([C:33]([O:35][CH3:36])=[O:34])[CH:30]=[CH:29][CH:28]=1.[I-].[Na+]>CN(C=O)C.O>[Cl:3][C:4]1[CH:5]=[C:6]([CH:11]2[O:17][CH2:16][CH2:15][N:14]([C:18]([O:20][C:21]([CH3:22])([CH3:24])[CH3:23])=[O:19])[CH2:13][CH:12]2[O:25][C:27]2[CH:28]=[CH:29][CH:30]=[C:31]([C:33]([O:35][CH3:36])=[O:34])[N:32]=2)[CH:7]=[CH:8][C:9]=1[Cl:10]

Komponenten

7

Edukt 4

HCID 5238Sodium IodideHCID 24758Sodium hydrideHCID 242723Methyl 6-chloropicolinateHCID 66975075tert-butyl (6RS,7SR)-7-(3,4-dichlorophenyl)-6-hydroxy-1,4-oxazepane-4-carboxylate

Produkt 1

HCID 66976194HCID 66976194, VerbindungAusbeute 37,7 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

Under ice-cooling, sodium hydride (60% in oil, 53 mg) was added to a solution of tert-butyl (6RS,7SR)-7-(3,4-dichlorophenyl)-6-hydroxy-1,4-oxazepane-4-carboxylate (400 mg) in DMF (5 mL). After stirring at room temperature for 20 min, methyl 6-chloropicolinate (280 mg) and sodium iodide (330 mg) were added, and the mixture was stirred at the same temperature for 1 hr. Water was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The extract was washed with brine, and dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography to give the title compound (207 mg).

Aufarbeitung

  1. temperatureUnder ice-cooling
  2. stirringthe mixture was stirred at the same temperature for 1 hr
  3. extractionthe mixture was extracted with ethyl acetate
  4. washThe extract was washed with brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. customThe solvent was evaporated under reduced pressure
  7. customThe residue was purified by silica gel column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-035657dbe8bf48f9af30c12d3cdf11f7
Quelldatensatz
uspto-grants-2014_05
Patentnummer
US08722662B2

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