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

HRID 467744

反応式

HRID 467744 の反応式
[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]

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

反応条件

温度
75 °C

実験手順

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%).

後処理

  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

出典と根拠

ORDレコード
ord-495a9bd1d11a4de7a97999cd4bc09afd
出典データセット
uspto-grants-2014_01
特許番号
US08623866B2

関連ノート

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