Reacción #1244272

ord-46d5f838c0014fccadf552da580c4195

Ecuación de reacción

O=C(Cn1ccnc1[N+](=O)[O-])NCc1cn(CCO)nn1
alcohol
O=C(Cn1ccnc1[N+](=O)[O-])NCc1cn(CCO)nn1
N-((1-(2-Hydroxyethyl)-1H-1,2,3-triazol-4-yl)methyl)-2-(2-nitro-1H-imidazol-1-yl)acetamide
Cc1ccc(S(=O)(=O)OS(=O)(=O)c2ccc(C)cc2)cc1
Ts2O
Cc1ccc(S(=O)(=O)OCCn2cc(CNC(=O)Cn3ccnc3[N+](=O)[O-])nn2)cc1
21
Rendimiento 34.1%
Cc1ccc(S(=O)(=O)OCCn2cc(CNC(=O)Cn3ccnc3[N+](=O)[O-])nn2)cc1
2-(4-((2-(2-Nitro-1H-imidazol-1-yl)acetamido)methyl)-1H-1,2,3-triazol-1-yl)ethyl 4-methylbenzenesulfonate
Rendimiento 34.1%

Disolventes

Condiciones de reacción

Condiciones detalladas
See reaction.notes.procedure_details.

Tratamiento posterior

  1. 1
    ConcentraciónThe reaction was then concentrated to dryness
  2. 2
    Otropurified on a silica gel cartridge

Procedimiento

To a round bottom flask was added the alcohol 20 (106 mg, 0.359 mmol), TEA (36.3 mg, 0.359 mmol) and DCM (10 mL). Ts2O (117 mg, 0.359 mmol) was added in one portion. The reaction was stirred at RT for 4 hrs. The reaction was then concentrated to dryness and purified on a silica gel cartridge using EtOAc:Hex as the eluent to afford 55 mg (34% yield) of 21 as a white solid. Mass Spec (lo-res): Calc'd for C17H19N7O6S: 449.11. found: 450.1 (M+H).

Fuente

DOI: 10.6084/m9.figshare.5104873.v1Patente: US07807394B2uspto-grants-2010_10