Hydroxyamine hydrochloride → 6-Benzoylamino-6-(2-naphthyl)hexanohydroxamic acid
Reaction equation
[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]=1Participants
6
Procedure
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).
Workup
- distillationthe methanol was distilled off under reduced pressure
- extractionextracted with ethyl acetate
- dry with materialThe extract was dried over anhydrous sodium sulfate
- concentrationconcentrated
- customthe crude residue was purified by silica gel column chromatography (ethyl acetate-hexane=2:1)
Sources & evidence
- ORD record
- ord-ad20eeff06cb4630af27938fcea5c5af
- Source dataset
- uspto-grants-1998_09
- Patent number
- US05804601
Reaction notes
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