Hydroxyamine hydrochloride → 6-Benzoylamino-6-(2-naphthyl)hexanohydroxamic acid

HRID 2393191Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2393191
[C:1]([NH:9][CH:10]([C:20]1[CH:29]=[CH:28][C:27]2[C:22](=[CH:23][CH:24]=[CH:25][CH:26]=2)[CH:21]=1)[CH2:11][CH2:12][CH2:13][CH2:14][C:15](OCC)=[O:16])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl.[NH2:31][OH:32].C[O-].[Na+].CO>CO.O>[C:1]([NH:9][CH:10]([C:20]1[CH:29]=[CH:28][C:27]2[C:22](=[CH:23][CH:24]=[CH:25][CH:26]=2)[CH:21]=1)[CH2:11][CH2:12][CH2:13][CH2:14][C:15]([NH:31][OH:32])=[O:16])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Komponenten

6

Edukt 3

HCID 443297Hydroxyamine hydrochlorideHCID 18979261HCID 18979261, VerbindungHCID 23694274Sodium methanolate methanol

Produkt 1

HCID 189791296-Benzoylamino-6-(2-naphthyl)hexanohydroxamic acidAusbeute 41,4 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 887MethanolLösungsmittelHCID 962WaterLösungsmittel

Versuchsvorschrift

Ethyl 6-benzoylamino-6-(2-naphthyl)hexanoate (Reference Example 25) (0.8 g) and hydroxylamine hydrochloride (0.71 g) were suspended in methanol. To this suspension (4.2 ml) was added 4.9N sodium methoxide/methanol (4.9 ml) and the mixture was stirred at room temperature for 2 hours. This reaction mixture was diluted with water and the methanol was distilled off under reduced pressure. The residue was acidified with 3N HCl and extracted with ethyl acetate. The extract was dried over anhydrous sodium sulfate and concentrated and the crude residue was purified by silica gel column chromatography (ethyl acetate-hexane=2:1) to provide the title compound (0.32 g).

Aufarbeitung

  1. distillationthe methanol was distilled off under reduced pressure
  2. extractionextracted with ethyl acetate
  3. dry with materialThe extract was dried over anhydrous sodium sulfate
  4. concentrationconcentrated
  5. customthe crude residue was purified by silica gel column chromatography (ethyl acetate-hexane=2:1)

Quellen und Nachweise

ORD-Eintrag
ord-ad20eeff06cb4630af27938fcea5c5af
Quelldatensatz
uspto-grants-1998_09
Patentnummer
US05804601

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