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

HRID 1278935ノート

反応式

HRID 1278935 の反応式
[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]

参加物

5

反応物 2

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

生成物 1

HCID 2775318Methyl (5-methyl-2-phenyl-1,3-oxazol-4-yl)acetate収率 97.71%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 1140Toluene溶媒

反応条件

温度
87.5 °C

実験手順

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%).

後処理

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

出典と根拠

ORDレコード
ord-c574d0aae5794497b1d4c376afb57b29
出典データセット
uspto-grants-2002_09
特許番号
US06444827B1

反応ノート

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