Triethylamine → N-hydroxy-N-(1-hydroxy-2-naphthyl)-4-methoxycarbonylbutanamide

HRID 1886257

Reaktionsgleichung

Reaktionsgleichung von HRID 1886257
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]

Komponenten

7

Edukt 4

HCID 8471TriethylamineHCID 73917Monomethyl glutarateHCID 516920Potassium bisulfateHCID 85613850HCID 85613850, Verbindung

Produkt 1

HCID 9882881N-hydroxy-N-(1-hydroxy-2-naphthyl)-4-methoxycarbonylbutanamideAusbeute 56 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

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.

Aufarbeitung

  1. extractionthe mixture extracted with CH2Cl2
  2. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  3. customthe solvent was removed under a reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-86ac543fa22749e18aab843bc2f5ad89
Quelldatensatz
uspto-grants-1992_09
Patentnummer
US05149859

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