2-Nitroimidazole → HCID 11192185, compound

HRID 1609428Notes

Reaction equation

HRID 1609428 reaction equation
[N+:1]([C:4]1[NH:5][CH:6]=[CH:7][N:8]=1)([O-:3])=[O:2].Br[C@@:10]1([O:33][C@H:32]([CH2:34][O:35][C:36](=[O:43])[C:37]2[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=2)[C@@H:22]([O:23][C:24](=[O:31])[C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[C@@H:12]1[O:13][C:14](=[O:21])[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)O>C(#N)C>[C:14]([O:13][C@H:12]1[C@H:22]([O:23][C:24](=[O:31])[C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[C@@H:32]([CH2:34][O:35][C:36](=[O:43])[C:37]2[CH:38]=[CH:39][CH:40]=[CH:41][CH:42]=2)[O:33][C@H:10]1[N:5]1[CH:6]=[CH:7][N:8]=[C:4]1[N+:1]([O-:3])=[O:2])(=[O:21])[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1

Participants

4

Reactant 2

HCID 107012-NitroimidazoleHCID 54246110HCID 54246110, compound

Product 1

HCID 11192185HCID 11192185, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

The coupling procedure of Sakaguchi (17) (12) was modified to give a higher yield and selective formation of the β-anomer. 2-Nitroimidazole (118 mg; 1.05 mmol) was added to a stirred solution of 1-bromo-2,3,5-tri-O-benzoyl-α-D-arabinofuranose (500 mg; 0.95 mmol) and mercuric cyanide (600 mg; 2.04 mmol) in dry acetonitrile (50 mL). The mixture was stirred for 6 hours at room temperature, after which the solvent was removed under vacuum. The residue was dissolved in dichloromethane (200 mL) and filtered. The filtrate was washed successively with saturated aqueous sodium hydrogen carbonate solution, 30% aqueous potassium iodide, and water, then dried over anhydrous magnesium sulfate. The solvent was evaporated under vacuum and the residue applied to a silica gel column and eluted with ethyl acetate:toluene=90:10 (v/v). The coupled product was recovered in 69% chemical yield (367 mg).

Workup

  1. customto give
  2. customa higher yield
  3. customafter which the solvent was removed under vacuum
  4. dissolutionThe residue was dissolved in dichloromethane (200 mL)
  5. filtrationfiltered
  6. washThe filtrate was washed successively with saturated aqueous sodium hydrogen carbonate solution, 30% aqueous potassium iodide, and water
  7. dry with materialdried over anhydrous magnesium sulfate
  8. customThe solvent was evaporated under vacuum
  9. washeluted with ethyl acetate
  10. customThe coupled product was recovered in 69%
  11. customchemical yield (367 mg)

Sources & evidence

ORD record
ord-70eb7d23dba3409790353aa37e5a0f61
Source dataset
uspto-grants-1995_03
Patent number
US05401490

Reaction notes

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