Réaction #1244263

ord-9da76c4d7e15453eb0313362fa643ed5

Équation de réaction

O=[N+]([O-])c1nccn1Cc1cn(CCO)nn1
alcohol
O=[N+]([O-])c1nccn1Cc1cn(CCO)nn1
2-(4-((2-Nitro-1H-imidazol-1-yl)methyl)-1H-1,2,3-triazol-1-yl)ethanol
Cc1ccc(S(=O)(=O)OS(=O)(=O)c2ccc(C)cc2)cc1
Ts2O
Cc1ccc(S(=O)(=O)OCCn2cc(Cn3ccnc3[N+](=O)[O-])nn2)cc1
12
Rendement 53.1%
Cc1ccc(S(=O)(=O)OCCn2cc(Cn3ccnc3[N+](=O)[O-])nn2)cc1
2-(4-((2-Nitro-1H-imidazol-1-yl)methyl)-1H-1,2,3-triazol-1-yl)ethyl 4-methylbenzenesulfonate
Rendement 53.1%

Solvants

Conditions de réaction

Conditions détaillées
See reaction.notes.procedure_details.

Traitement

  1. 1
    ConcentrationThe reaction was concentrated in vacuo
  2. 2
    Autrepurified on a silica gel cartridge

Mode opératoire

To a round bottom flask containing alcohol 11 (160 mg, 0.672 mmol), TEA (136 mg, 1.34 mmol) and DCM (5 mL) was added Ts2O (263 mg, 0.806 mmol). The reaction was stirred at RT for 4 hrs. TLC indicated that the reaction was complete. The reaction was concentrated in vacuo and purified on a silica gel cartridge using EtOAc:Hex as the eluent to afford 140 mg (53% yield) of 12 as a pale orange oil. Mass Spec (lo-res): Calc'd for C15H16N6O5S: 392.092. found: 393.10 (M+H).

Source

DOI: 10.6084/m9.figshare.5104873.v1Brevet: US07807394B2uspto-grants-2010_10