反应 #1857567

ord-20649e04a4304a5aa882a67bdf9a0197

反应方程式

O=C1CCC(=O)N1Cl
N-chlorosuccinimide
CC(C)(C)OC(=O)N1CCC(c2nc(C=NO)cs2)CC1
tert-butyl 4-{4-[(hydroxyimino)methyl]-1,3-thiazol-2-yl}piperidine-1-carboxylate
C=Cc1ccccc1O
2-vinylphenol
O=C([O-])O.[K+]
potassium hydrogencarbonate
CC(C)(C)OC(=O)N1CCC(c2nc(C3=NOC(c4ccccc4O)C3)cs2)CC1
tert-Butyl 4-{4-[5-(2-hydroxyphenyl)-4,5-dihydro-1,2-oxazol-3-yl]-1,3-thiazol-2-yl}piperidine-1-carboxylate

反应条件

温度
60°CELSIUS
详细条件
See reaction.notes.procedure_details.

后处理

  1. 1
    萃取extracted with ethyl acetate
  2. 2
    干燥The organic extracts were dried over sodium sulphate
  3. 3
    浓缩concentrated under reduced pressure
  4. 4
    其他The residue was purified by chromatography

实验过程

To a solution of tert-butyl 4-{4-[(hydroxyimino)methyl]-1,3-thiazol-2-yl}piperidine-1-carboxylate (3.46 g) and 2-vinylphenol (1.60 g) in ethyl acetate (50 ml) were added, at room temperature, potassium hydrogencarbonate (5.55 g) and N-chlorosuccinimide (1.78 g), and then one drop of water. After stirring at 60° C. overnight, the reaction mixture was admixed with ethyl acetate and water and extracted with ethyl acetate. The organic extracts were dried over sodium sulphate and concentrated under reduced pressure. The residue was purified by chromatography. This gave tert-butyl 4-{4-[5-(2-hydroxyphenyl)-4,5-dihydro-1,2-oxazol-3-yl]-1,3-thiazol-2-yl}piperidine-1-carboxylate (1.70 g).

来源

DOI: 10.6084/m9.figshare.5104873.v1专利: US09247748B2uspto-grants-2016_02