Ethyl Acetate → (S)-2-ethyl-7-methoxycarbonyl-3-oxo-3,4-dihydro-2H-1,4-benzoxazine

HRID 234906Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 234906
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([O:10][CH3:11])=[O:9])=[CH:4][C:3]=1[OH:12].C(OCC)(=O)C.C(=O)([O-])O.[Na+].Cl[C@H:25]([CH2:29][CH3:30])[C:26](Cl)=[O:27]>O>[CH2:29]([C@H:25]1[C:26](=[O:27])[NH:1][C:2]2[CH:7]=[CH:6][C:5]([C:8]([O:10][CH3:11])=[O:9])=[CH:4][C:3]=2[O:12]1)[CH3:30]

Komponenten

6

Edukt 4

HCID 8857Ethyl AcetateHCID 516892Sodium BicarbonateHCID 7020619Benzoic acid, 4-amino-3-hydroxy-, methyl esterHCID 7568786(R)-2-chlorobutyryl chloride

Produkt 1

HCID 10633499(S)-2-ethyl-7-methoxycarbonyl-3-oxo-3,4-dihydro-2H-1,4-benzoxazineAusbeute 88,9 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Versuchsvorschrift

To a solution of 2-amino-5-methoxycarbonylphenol [Tetrahedron, 46(15), 5177-5186 (1990)] (7.50 g) in a mixed solvent of ethyl acetate (60 ml) and water (60 ml) were added sodium hydrogen carbonate (5.20 g) and (R)-2-chlorobutyryl chloride (7.50 g) and the mixture was stirred at room temperature for 10 minutes. The organic layer was separated and the solvent was distilled off under reduced pressure. The resulting residue was dissolved in dimethylformamide (90 ml), to the solution was added potassium carbonate (6.20 g) and the mixture was stirred at room temperature overnight. Water was added to the reaction solution and the resulting crystals were taken by filtration to give (S)-2-ethyl-7-methoxycarbonyl-3-oxo-3,4-dihydro-2H-1,4-benzoxazine (9.38 g).

Aufarbeitung

  1. customThe organic layer was separated
  2. distillationthe solvent was distilled off under reduced pressure
  3. dissolutionThe resulting residue was dissolved in dimethylformamide (90 ml), to the solution
  4. additionwas added potassium carbonate (6.20 g)
  5. stirringthe mixture was stirred at room temperature overnight
  6. additionWater was added to the reaction solution
  7. filtrationthe resulting crystals were taken by filtration

Quellen und Nachweise

ORD-Eintrag
ord-b7323edc52714161a112813d18b22f56
Quelldatensatz
uspto-grants-1997_01
Patentnummer
US05597820

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