Sodium Carbonate → Methyl (5-methyl-2-phenyl-1,3-oxazol-4-yl)acetate

HRID 890347Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 890347
[C:1]([NH:9][CH:10]([C:16](=[O:18])[CH3:17])[CH2:11][C:12]([O:14][CH3:15])=[O:13])(=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(=O)([O-])[O-].[Na+].[Na+]>C1(C)C=CC=CC=1.O>[CH3:17][C:16]1[O:18][C:1]([C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=2)=[N:9][C:10]=1[CH2:11][C:12]([O:14][CH3:15])=[O:13]

Komponenten

5

Edukt 2

HCID 10340Sodium CarbonateHCID 13657848Methyl 3-benzamido-4-oxopentanoate2×

Produkt 1

HCID 2775318Methyl (5-methyl-2-phenyl-1,3-oxazol-4-yl)acetateAusbeute 97,7 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 1140TolueneLösungsmittel

Versuchsvorschrift

To β-methyl N-benzoyl-L-aspartate (compound [3]; 229.9 g) obtained in Example 1 were successively added toluene (1.2 L), acetic anhydride (346 mL), N-methylmorpholine (4.7 mL) and 4-dimethylaminopyridine (1.04 g) and the mixture was stirred at internal temperature of 55–0° C. for 4 hr to give a solution of methyl 3-benzoylamino-4-oxopentanoate (compound [4]) in toluene. Without isolating compound [4], p-toluenesulfonic acid monohydrate (31.8 g) was added to this solution of methyl 3-benzoylamino-4-oxopentanoate (compound [4]) in toluene. The mixture was stirred at 85–90° C. for 5 hr and cooled to room temperature. To the reaction mixture was added, with stirring, an aqueous solution of sodium carbonate (75.6 g) in water (303 mL), and the mixture was adjusted to pH 7–7.5. After standing still, the aqueous layer was removed and the organic layer was concentrated to give the title compound (compound [5]; 206.7 g, yield 97.7%).

Aufarbeitung

  1. additionTo the reaction mixture was added
  2. stirringwith stirring
  3. customthe aqueous layer was removed
  4. concentrationthe organic layer was concentrated

Quellen und Nachweise

ORD-Eintrag
ord-b3dd89ee235d4b57829dc7899a2d45f3
Quelldatensatz
uspto-grants-2006_02
Patentnummer
US06995271B2

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