Reaktion #1244272

ord-46d5f838c0014fccadf552da580c4195

Reaktionsgleichung

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
Ausbeute 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
Ausbeute 34.1%

Lösungsmittel

Reaktionsbedingungen

Detaillierte Bedingungen
See reaction.notes.procedure_details.

Aufarbeitung

  1. 1
    EinengenThe reaction was then concentrated to dryness
  2. 2
    Sonstigepurified on a silica gel cartridge

Vorschrift

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).

Quelle

DOI: 10.6084/m9.figshare.5104873.v1Patent: US07807394B2uspto-grants-2010_10