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

HRID 1278935Notes

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

Conditions

Temperature: 87.5 °C

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 55-60° 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-benzoylamino4-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 97.71%).

Workup

temperaturecooled to room temperature
additionTo the reaction mixture was added
stirringwith stirring
customthe aqueous layer was removed
concentrationthe organic layer was concentrated

Sources & evidence

ORD record: ord-c574d0aae5794497b1d4c376afb57b29
Source dataset: uspto-grants-2002_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06444827B1

Reaction notes

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