Sodium Acetate → HCID 23081163, compound

HRID 856364Notes

Reaction equation

HRID 856364 reaction equation
[Cl:1][C:2]1[NH:3][CH:4]=[C:5]([N+:7]([O-:9])=[O:8])[N:6]=1.[N:10]([CH2:13][CH:14]1[O:18][C:17](=[O:19])[N:16]([CH2:20][C:21]2([CH3:24])[CH2:23][O:22]2)[CH2:15]1)=[N+:11]=[N-:12].C([O-])(=O)C.[Na+]>C(O)C>[N:10]([CH2:13][CH:14]1[O:18][C:17](=[O:19])[N:16]([CH2:20][C:21]([OH:22])([CH3:23])[CH2:24][N:3]2[CH:4]=[C:5]([N+:7]([O-:9])=[O:8])[N:6]=[C:2]2[Cl:1])[CH2:15]1)=[N+:11]=[N-:12]

Participants

5

Reactant 3

HCID 517045Sodium AcetateHCID 23081542HCID 23081542, compoundHCID 178526855HCID 178526855, compound

Product 1

HCID 23081163HCID 23081163, compoundYield 75.1%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
70 °C

Procedure

A mixture of 2-chloro-4-nitro-1H-imidazole (350 mg, 2.37 mmol), 5-azidomethyl-3-(2-methyloxiran-2-ylmethyl)oxazolidin-2-one (500 mg, 2.37 mmol), sodium acetate (214 mg, 2.61 mmol) and ethanol (5 ml) was stirred at 70° C. for 8 hours. The reaction mixture was allowed to return to room temperature and concentrated under reduced pressure. To the residue, water was added, and the solution was extracted with methylene chloride. The organic phase was dried over sodium sulfate and then filtered. The filtrate was concentrated under reduced pressure, and the residue was purified by silica gel column chromatography (n-hexane/ethyl acetate=1/2) to afford 5-azidomethyl-3-[3-(2-chloro-4-nitroimidazol-1-yl)-2-hydroxy-2-methylpropyl]oxazolidin-2-one (640 mg, yield 75%) as a light yellow oil.

Workup

  1. customto return to room temperature
  2. concentrationconcentrated under reduced pressure
  3. additionTo the residue, water was added
  4. extractionthe solution was extracted with methylene chloride
  5. dry with materialThe organic phase was dried over sodium sulfate
  6. filtrationfiltered
  7. concentrationThe filtrate was concentrated under reduced pressure
  8. customthe residue was purified by silica gel column chromatography (n-hexane/ethyl acetate=1/2)

Sources & evidence

ORD record
ord-e13aa1c913334d0485d8505521a7a851
Source dataset
uspto-grants-2007_08
Patent number
US07262212B2

Reaction notes

Loading…