Pyridine → HCID 178502569, compound

HRID 1110969Notes

Reaction equation

HRID 1110969 reaction equation
[OH:1][CH2:2][CH2:3][NH:4][C:5](=[O:18])[C:6]([F:17])([F:16])[CH2:7][C:8]1[N:9]=[C:10]([N+:13]([O-:15])=[O:14])[NH:11][CH:12]=1.N1C=CC=CC=1.Cl[C:26]([O:28][CH3:29])=[O:27]>C(Cl)(Cl)Cl>[N+:13]([C:10]1[NH:11][CH:12]=[C:8]([CH2:7][C:6]([F:17])([F:16])[C:5]([NH:4][CH2:3][CH2:2][O:1][C:26]([O:28][CH3:29])=[O:27])=[O:18])[N:9]=1)([O-:15])=[O:14]

Participants

5

Reactant 3

HCID 1049PyridineHCID 6586Methyl chloroformateHCID 178523465HCID 178523465, compound

Product 1

HCID 178502569HCID 178502569, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent2×

Procedure

3-(2'-Nitroimidazolyl)-2,2-difluoropropionic acid hydroxyethylamide (6.0 g, 22.7 mmol) was dissolved in a solvent mixture of methyl chloroformate (30 ml) and chloroform (30 ml) and cooled by ice. To the solution, a solution of pyridine (6.0 ml) in chloroform (30 ml) was dropwise added over 2 hours. The completion of the reaction was confirmed by thin-layer chromatography. Then, the reaction solution was washed with dilute hydrochloric acid and water, dried over magnesium sulfate, concentrated and subjected to silica gel column chromatography to obtain methyl 3-(2'-nitroimidazolyl)-2,2-difluoropropionamidoethoxyformate (6.89 g). m.p. 50.5°-52.5° C.

Workup

  1. temperaturecooled by ice
  2. washThen, the reaction solution was washed with dilute hydrochloric acid and water
  3. dry with materialdried over magnesium sulfate
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-96ce97bd88bd40349b72b9220038ee3d
Source dataset
uspto-grants-1990_12
Patent number
US04977273

Reaction notes

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