Pyridine → Methyl 3-(5-phenyl-1,3,4-oxadiazol-2-yl)propanoate

HRID 2368601노트

반응식

HRID 2368601 반응식
S(Cl)(Cl)=O.[C:5]([NH:13][NH:14][C:15](=[O:22])[CH2:16][CH2:17][C:18]([O:20][CH3:21])=[O:19])(=O)[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1.N1C=CC=CC=1>O1CCCC1>[C:6]1([C:5]2[O:22][C:15]([CH2:16][CH2:17][C:18]([O:20][CH3:21])=[O:19])=[N:14][N:13]=2)[CH:7]=[CH:8][CH:9]=[CH:10][CH:11]=1

참가 물질

5

반응물 3

HCID 1049PyridineHCID 24386Thionyl ChlorideHCID 569517Methyl 4-(2-benzoylhydrazino)-4-oxobutanoate

생성물 1

HCID 57600262Methyl 3-(5-phenyl-1,3,4-oxadiazol-2-yl)propanoate수율 72%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

Thionyl chloride (0.34 mL, 4.7 mmol) was added to the mixture of methyl 4-(2-benzoylhydrazino)-4-oxobutanoate (900 mg, 4 mmol), Pyridine (0.87 mL, 0.011 mol) in tetrahydrofuran (20 mL) at room temperature. After stirring for 3 hours, the reaction mixture was concentrated. The residue was mixed with toluene (20 mL) and refluxed overnight. The reaction was diluted with water and extracted with ethyl acetate three times. The combined organic layers were dried with sodium sulfate, filtered, and concentrated in vacuo. The residue was purified by flash column chromatography to yield the desired product (600 mg, 72%). LCMS calculated for C12H13N2O3 (M+H): 233.1. Found: 233.1.

후처리

  1. concentrationthe reaction mixture was concentrated
  2. additionThe residue was mixed with toluene (20 mL)
  3. temperaturerefluxed overnight
  4. additionThe reaction was diluted with water
  5. extractionextracted with ethyl acetate three times
  6. dry with materialThe combined organic layers were dried with sodium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo
  9. customThe residue was purified by flash column chromatography

출처 및 근거

ORD 기록
ord-ad01e629fba249618104007c37f20423
출처 데이터셋
uspto-grants-2014_04
특허 번호
US08703783B2

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