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

HRID 1278935노트

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HRID 1278935 반응식
[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]

참가 물질

5

반응물 2

HCID 10340Sodium CarbonateHCID 13657848Methyl 3-benzamido-4-oxopentanoate2회

생성물 1

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

시약·촉매·용매 2

HCID 962Water용매HCID 1140Toluene용매

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온도
87.5 °C

실험 절차

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%).

후처리

  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

출처 및 근거

ORD 기록
ord-c574d0aae5794497b1d4c376afb57b29
출처 데이터셋
uspto-grants-2002_09
특허 번호
US06444827B1

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