반응 #1857571

ord-0fbfa7875c6d42d29f4137f5fca1ee7f

반응 방정식

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=Cc1ccccc1[N+](=O)[O-]
1-nitro-2-vinylbenzene
O=C([O-])O.[K+]
potassium hydrogencarbonate
CC(C)(C)OC(=O)N1CCC(c2nc(C3=NOC(c4ccccc4[N+](=O)[O-])C3)cs2)CC1
tert-Butyl 4-{4-[5-(2-nitrophenyl)-4,5-dihydro-1,2-oxazol-3-yl]-1,3-thiazol-2-yl}piperidine-1-carboxylate

반응 조건

온도
60°CELSIUS
상세 조건
See reaction.notes.procedure_details.

후처리

  1. 1
    추출extracted with ethyl acetate
  2. 2
    건조The organic extracts were dried over sodium sulphate
  3. 3
    농축concentrated under reduced pressure
  4. 4
    기타The residue was purified by chromatography

실험 절차

To a solution of tert-butyl 4-{4-[(hydroxyimino)methyl]-1,3-thiazol-2-yl}piperidine-1-carboxylate (2.80 g) and 1-nitro-2-vinylbenzene (1.60 g) in ethyl acetate (50 ml) were added, at room temperature, potassium hydrogencarbonate (4.50 g) and N-chlorosuccinimide (1.44 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-nitrophenyl)-4,5-dihydro-1,2-oxazol-3-yl]-1,3-thiazol-2-yl}piperidine-1-carboxylate (2.10 g).

출처

DOI: 10.6084/m9.figshare.5104873.v1특허: US09247748B2uspto-grants-2016_02