Ethyl Acetate → 3-(Cyclopropylcarbamoyl)-isoxazole-4-carboxylic acid ethyl ester

HRID 467744

반응식

HRID 467744 반응식
[CH:1]1([NH:4][C:5](=[O:10])[C:6](Cl)=[N:7][OH:8])[CH2:3][CH2:2]1.[CH2:11]([O:13][C:14](=[O:20])/[CH:15]=[CH:16]/N(C)C)[CH3:12].C(OCC)(=O)C>C1COCC1>[CH2:11]([O:13][C:14]([C:15]1[C:6]([C:5](=[O:10])[NH:4][CH:1]2[CH2:3][CH2:2]2)=[N:7][O:8][CH:16]=1)=[O:20])[CH3:12]

참가 물질

5

반응물 3

HCID 8857Ethyl AcetateHCID 5369162Ethyl trans-3-dimethylaminoacrylateHCID 85344446N-cyclopropyl-2-chloro-2-hydroxyimino-acetamide

생성물 1

HCID 700979003-(Cyclopropylcarbamoyl)-isoxazole-4-carboxylic acid ethyl ester

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

반응 조건

온도
75 °C

실험 절차

A mixture of N-cyclopropyl-2-chloro-2-hydroxyimino-acetamide (2 g, 12.3 mmol) and (E)-3-(dimethylamino)-acrylic acid ethyl ester (1.76 ml, 12.3 mmol) in THF (25 ml) was heated at 75° C. for 2 h. The reaction was then cooled to r.t., poured into 100 mL ethyl acetate and extracted with 1 M HCl. The aqueous layers were back-extracted with ethyl acetate. The organic phase was washed with water and brine, dried and evaporated. The product was obtained after purification by silica gel chromatography using a heptane/ethyl acetate gradient as light yellow solid (1.6 g, 58%).

후처리

  1. temperatureThe reaction was then cooled to r.t.
  2. extractionextracted with 1 M HCl
  3. extractionThe aqueous layers were back-extracted with ethyl acetate
  4. washThe organic phase was washed with water and brine
  5. customdried
  6. customevaporated
  7. customThe product was obtained
  8. customafter purification by silica gel chromatography

출처 및 근거

ORD 기록
ord-495a9bd1d11a4de7a97999cd4bc09afd
출처 데이터셋
uspto-grants-2014_01
특허 번호
US08623866B2

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