تفاعل #1857574

ord-2f407bfd54fa48fb9962006b64230ff4

معادلة التفاعل

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=Cc1ccccc1OCC1CCCCC1
1-(cyclohexylmethoxy)-2-vinylbenzene
O=C([O-])O.[K+]
potassium hydrogencarbonate
CC(C)(C)OC(=O)N1CCC(c2nc(C3=NOC(c4ccccc4OCC4CCCCC4)C3)cs2)CC1
tert-Butyl 4-(4-{5-[2-(cyclohexylmethoxy)phenyl]-4,5-dihydro-1,2-oxazol-3-yl}-1,3-thiazol-2-yl)piperidine-1-carboxylate

ظروف التفاعل

درجة الحرارة
60°CELSIUS
الظروف التفصيلية
See reaction.notes.procedure_details.

المعالجة

  1. 1
    استخلاصextracted with ethyl acetate
  2. 2
    تجفيفThe organic extracts were dried over sodium sulphate
  3. 3
    تركيزconcentrated under reduced pressure
  4. 4
    أخرىThe residue was purified by chromatography

الإجراء التجريبي

To a solution of tert-butyl 4-{4-[(hydroxyimino)methyl]-1,3-thiazol-2-yl}piperidine-1-carboxylate (2.90 g) and 1-(cyclohexylmethoxy)-2-vinylbenzene (2.40 g) in ethyl acetate (300 ml) were added, at room temperature, potassium hydrogencarbonate (4.60 g) and N-chlorosuccinimide (1.48 g), and then one drop of water. The reaction mixture was stirred at 60° C. for 6 h, then 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-(cyclohexylmethoxy)phenyl]-4,5-dihydro-1,2-oxazol-3-yl}-1,3-thiazol-2-yl)piperidine-1-carboxylate (3.40 g).

المصدر

DOI: 10.6084/m9.figshare.5104873.v1براءة الاختراع: US09247748B2uspto-grants-2016_02