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

HRID 890347Notes

Reaction equation

HRID 890347 reaction equation
[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]

Participants

5

Reactant 2

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

Product 1

HCID 2775318Methyl (5-methyl-2-phenyl-1,3-oxazol-4-yl)acetateYield 97.7%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 1140TolueneSolvent

Procedure

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%).

Workup

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

Sources & evidence

ORD record
ord-b3dd89ee235d4b57829dc7899a2d45f3
Source dataset
uspto-grants-2006_02
Patent number
US06995271B2

Reaction notes

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