Triethylamine → N-hydroxy-N-(1-hydroxy-2-naphthyl)-4-methoxycarbonylbutanamide
Reaction equation
Cl.[OH:2][C:3]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[CH:6]=[CH:5][C:4]=1[NH:13][OH:14].C(N(CC)CC)C.[CH3:22][O:23][C:24]([CH2:26][CH2:27][CH2:28][C:29](O)=[O:30])=[O:25].OS([O-])(=O)=O.[K+]>C1COCC1.O>[OH:14][N:13]([C:4]1[CH:5]=[CH:6][C:7]2[C:12](=[CH:11][CH:10]=[CH:9][CH:8]=2)[C:3]=1[OH:2])[C:29](=[O:30])[CH2:28][CH2:27][CH2:26][C:24]([O:23][CH3:22])=[O:25]Participants
7
Reactant 4
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 0 °C
Procedure
Into a solution of 2 g (9.5 mmol) of 1-hydroxy-2-naphthylhydroxylamine hydrochloride in THF (10 ml) and water (2 ml) was added 2 ml (14.2 mmol) of triethylamine, the mixture was cooled to 0° C., and 395 mg (2.4 mmol) of acid chloride of 4-methoxycarbonylbutanoic acid was added followed by stirring at room temperature. Aqueous KHSO4 was then added and the mixture extracted with CH2Cl2. The organic layer was dried over anhydrous magnesium sulfate, the solvent was removed under a reduced pressure, and the residue subjected to silica gel column chromatography to give 405 mg (56%) of a hydroxyamic acid derivative.
Workup
- extractionthe mixture extracted with CH2Cl2
- dry with materialThe organic layer was dried over anhydrous magnesium sulfate
- customthe solvent was removed under a reduced pressure
Sources & evidence
- ORD record
- ord-86ac543fa22749e18aab843bc2f5ad89
- Source dataset
- uspto-grants-1992_09
- Patent number
- US05149859
Reaction notes
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