Hydrochloric Acid → 1-(2,2-Dihydroxymethyl-3-fluoropropyl)-2-nitroimidazole

HRID 514621Notes

Reaction equation

HRID 514621 reaction equation
CC1(C)[O:7][CH2:6][C:5]([CH2:17][F:18])([CH2:8][N:9]2[CH:13]=[CH:12][N:11]=[C:10]2[N+:14]([O-:16])=[O:15])[CH2:4][O:3]1.Cl>CO>[OH:3][CH2:4][C:5]([CH2:6][OH:7])([CH2:17][F:18])[CH2:8][N:9]1[CH:13]=[CH:12][N:11]=[C:10]1[N+:14]([O-:16])=[O:15]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 894722902,2-dimethyl-5-fluoromethyl-5-[(2-nitro-1H-imidazol-1-yl)methyl]-1,3-dioxane

Product 1

HCID 894722911-(2,2-Dihydroxymethyl-3-fluoropropyl)-2-nitroimidazoleYield 98.5%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
80 °C

Procedure

56.3 mg (0.206 mmol equivalents) of 2,2-dimethyl-5-fluoromethyl-5-[(2-nitro-1H-imidazol-1-yl)methyl]-1,3-dioxane was dissolved in 2 mL of methanol, 2 mL of 1 mol/L hydrochloric acid was added thereto, and the mixture was heated at 80° C. for 2 hours. After completion of the reaction, the reaction liquid was cooled to room temperature (25° C.), the solvent was then removed by distillation, and the obtained crude product was washed with ethyl acetate to give 47.3 mg (0.203 mmol equivalents) of 1-(2,2-dihydroxymethyl-3-fluoropropyl)-2-nitroimidazole (FIG. 2, Step 2).

Workup

  1. customAfter completion of the reaction
  2. customthe reaction liquid
  3. temperaturewas cooled to room temperature (25° C.)
  4. customthe solvent was then removed by distillation
  5. customthe obtained crude product
  6. washwas washed with ethyl acetate

Sources & evidence

ORD record
ord-5446a3fe76d742bc88c1b9cda4b005b2
Source dataset
uspto-grants-2015_08
Patent number
US09107964B2

Reaction notes

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