Reaction #1244276

ord-e390245c0a84494f97c13be61e1e25ed

Reaction equation

CC(=O)OCC(CO)N=[N+]=[N-]
Compound 24
CC(=O)OCC(CO)N=[N+]=[N-]
2-Azido-3-hydroxypropyl acetate
CC#Cn1ccnc1[N+](=O)[O-]
1-propynyl-2-nitroimidazole
→
CC(=O)OCC(CO)n1cc(Cn2ccnc2[N+](=O)[O-])nn1
white solid
Yield 52.0%
CC(=O)OCC(CO)n1cc(Cn2ccnc2[N+](=O)[O-])nn1
3-Hydroxy-2-(4-((2-nitro-1H-imidazol-1-yl)methyl)-1H-1,2,3-triazol-1-yl)propyl acetate
Yield 52.0%

Reactants

CC(=O)OCC(CO)N=[N+]=[N-]
Compound 24
CC(=O)OCC(CO)N=[N+]=[N-]
2-Azido-3-hydroxypropyl acetate
CC#Cn1ccnc1[N+](=O)[O-]
1-propynyl-2-nitroimidazole

Reagents

None

Conditions

Temperature
60°CELSIUS
Detailed conditions
See reaction.notes.procedure_details.

Workup

  1. 1
    OtherThe resultant solid was purified on a silica gel cartridge

Procedure

A vial containing Compound 24 (500 mg, 3.14 mmol) and 1-propynyl-2-nitroimidazole (475 mg, 3.14 mmol) was heated at 60° C. overnight. The resultant solid was purified on a silica gel cartridge using EtOAc:Hex as the eluent to afford 504 mg (52% yield) of a white solid.

Source

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