乙酸乙酯 → 3-(Cyclopropylcarbamoyl)-isoxazole-4-carboxylic acid ethyl ester

HRID 2368341

反应方程式

HRID 2368341 反应方程式
[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]

参与物

5

反应物 3

HCID 8857乙酸乙酯HCID 5369162N,N-二甲氨基丙烯酸乙酯HCID 85344446N-cyclopropyl-2-chloro-2-hydroxyimino-acetamide

产物 1

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

试剂、催化剂与溶剂 1

HCID 8028四氢呋喃溶剂

反应条件

温度
75 °C

实验过程

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%).

后处理

  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

来源与证据

ORD记录
ord-c0bc2d58bbb842d892b8d1461e1e93ad
来源数据集
uspto-grants-2014_04
专利号
US08703768B2

关联笔记

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