Methanol → (Z)-2-(furan-2-carbonylamino)-3-(5-phenyl-2-furyl)prop-2-enoic Acid

HRID 1823955

반응식

HRID 1823955 반응식
[OH-:1].[Na+].O.[O:4]1[CH:8]=[CH:7][CH:6]=[C:5]1[C:9]1[O:10][C:11](=[O:26])/[C:12](=[CH:14]/[C:15]2[O:16][C:17]([C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)=[CH:18][CH:19]=2)/[N:13]=1.CO>CC(C)=O>[O:4]1[CH:8]=[CH:7][CH:6]=[C:5]1[C:9]([NH:13]/[C:12](=[CH:14]\[C:15]1[O:16][C:17]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)=[CH:18][CH:19]=1)/[C:11]([OH:10])=[O:26])=[O:1]

참가 물질

6

반응물 4

HCID 887MethanolHCID 962WaterHCID 14798Sodium HydroxideHCID 22148173(4Z)-2-(2-furyl)-4-[(5-phenyl-2-furyl)methylene]-1,3-oxazol-5(4H)-one

생성물 1

HCID 10358813(Z)-2-(furan-2-carbonylamino)-3-(5-phenyl-2-furyl)prop-2-enoic Acid

시약·촉매·용매 1

HCID 180Acetone용매

반응 조건

온도
75 °C

실험 절차

1N NaOH (100 μL) and H2O (500 μL) is added to a solution of (4Z)-2-(2-furyl)-4-[(5-phenyl-2-furyl)methylene]-1,3-oxazol-5(4H)-one (10 mg, 0.0327 mmol), prepared as described above, in acetone (1 mL). The reaction mixture is heated to 75° C. for one hour and then cooled to 25° C. The crude mixture is loaded onto a QAX column, which was pre-treated with MeOH. After 2 minutes the column is washed with MeOH and the product is eluted with 3% HCl/MeOH. Subsequently, the column is washed with MeOH (2 mL) and the combined washings are concentrated under reduced pressure to provide 9.5 mg of (2Z)-2-(2-furoylamino)-3-(5-phenyl-2-furyl)prop-2-enoic acid.

후처리

  1. customprepared
  2. temperaturecooled to 25° C
  3. washAfter 2 minutes the column is washed with MeOH
  4. washthe product is eluted with 3% HCl/MeOH
  5. washSubsequently, the column is washed with MeOH (2 mL)
  6. concentrationthe combined washings are concentrated under reduced pressure

출처 및 근거

ORD 기록
ord-10ca92942e8147eb8665ae8b5bdcf3f2
출처 데이터셋
uspto-grants-2006_05
특허 번호
US07041690B2

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